JPWO2015056811A1 - Tetrazolinone compounds and uses thereof - Google Patents
Tetrazolinone compounds and uses thereof Download PDFInfo
- Publication number
- JPWO2015056811A1 JPWO2015056811A1 JP2015542920A JP2015542920A JPWO2015056811A1 JP WO2015056811 A1 JPWO2015056811 A1 JP WO2015056811A1 JP 2015542920 A JP2015542920 A JP 2015542920A JP 2015542920 A JP2015542920 A JP 2015542920A JP WO2015056811 A1 JPWO2015056811 A1 JP WO2015056811A1
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- ome
- methyl
- atom
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- JXBKZAYVMSNKHA-UHFFFAOYSA-N 1h-tetrazol-1-ium-5-olate Chemical class OC=1N=NNN=1 JXBKZAYVMSNKHA-UHFFFAOYSA-N 0.000 title claims description 14
- -1 tetrazolinone compound Chemical class 0.000 claims abstract description 938
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 227
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 143
- 125000004429 atom Chemical group 0.000 claims abstract description 74
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 50
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract description 39
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 23
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 23
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 21
- 125000005843 halogen group Chemical group 0.000 claims description 51
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
- 239000003795 chemical substances by application Substances 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 34
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 30
- 125000005347 halocycloalkyl group Chemical group 0.000 claims description 20
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 12
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 10
- 125000006643 (C2-C6) haloalkenyl group Chemical group 0.000 claims description 10
- 125000006644 (C2-C6) haloalkynyl group Chemical group 0.000 claims description 10
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 10
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
- 125000005109 alkynylthio group Chemical group 0.000 claims description 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 9
- 125000006771 (C1-C6) haloalkylthio group Chemical group 0.000 claims description 9
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 9
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000005108 alkenylthio group Chemical group 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 8
- 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 8
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 7
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 6
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 5
- 125000004771 (C1-C4) haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 125000004749 (C1-C6) haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 5
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 5
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000001769 aryl amino group Chemical group 0.000 claims description 5
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 5
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 5
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 5
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 5
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 5
- 125000005241 heteroarylamino group Chemical group 0.000 claims description 5
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 4
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 4
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 239000002689 soil Substances 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 370
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 213
- 238000006243 chemical reaction Methods 0.000 description 208
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 174
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 162
- 239000000203 mixture Substances 0.000 description 127
- 238000004519 manufacturing process Methods 0.000 description 123
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 108
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 81
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 79
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 239000011541 reaction mixture Substances 0.000 description 67
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 64
- 239000012044 organic layer Substances 0.000 description 61
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 60
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 56
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 52
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 50
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 50
- 229910052760 oxygen Inorganic materials 0.000 description 50
- 239000001301 oxygen Substances 0.000 description 50
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
- 239000002904 solvent Substances 0.000 description 46
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 44
- 238000005160 1H NMR spectroscopy Methods 0.000 description 43
- 239000002585 base Substances 0.000 description 43
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 40
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 40
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 40
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 39
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 38
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 37
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 36
- 239000003054 catalyst Substances 0.000 description 35
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 35
- 125000001309 chloro group Chemical group Cl* 0.000 description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
- 201000010099 disease Diseases 0.000 description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 30
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 28
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- 229910000027 potassium carbonate Inorganic materials 0.000 description 28
- 235000011181 potassium carbonates Nutrition 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000005859 coupling reaction Methods 0.000 description 27
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 26
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 26
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 26
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 25
- 235000017557 sodium bicarbonate Nutrition 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000010438 heat treatment Methods 0.000 description 24
- 238000010992 reflux Methods 0.000 description 24
- 238000010898 silica gel chromatography Methods 0.000 description 23
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 22
- 238000004587 chromatography analysis Methods 0.000 description 22
- 150000008282 halocarbons Chemical class 0.000 description 22
- 230000035484 reaction time Effects 0.000 description 22
- 238000001953 recrystallisation Methods 0.000 description 22
- 229920006395 saturated elastomer Polymers 0.000 description 22
- 239000008096 xylene Substances 0.000 description 22
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 21
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 21
- 101150023830 PYR1 gene Proteins 0.000 description 21
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 238000001035 drying Methods 0.000 description 21
- 150000002170 ethers Chemical class 0.000 description 21
- 238000000605 extraction Methods 0.000 description 21
- 150000002825 nitriles Chemical class 0.000 description 21
- 239000003960 organic solvent Substances 0.000 description 21
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 20
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 19
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 19
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 19
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 19
- 229910000024 caesium carbonate Inorganic materials 0.000 description 18
- 229930195733 hydrocarbon Natural products 0.000 description 18
- 150000002430 hydrocarbons Chemical class 0.000 description 18
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 150000002148 esters Chemical class 0.000 description 17
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 15
- 238000004821 distillation Methods 0.000 description 15
- 230000002140 halogenating effect Effects 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 14
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 14
- 229910052783 alkali metal Inorganic materials 0.000 description 14
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 14
- 150000008041 alkali metal carbonates Chemical class 0.000 description 14
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 14
- 150000007530 organic bases Chemical class 0.000 description 14
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 14
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 150000003462 sulfoxides Chemical class 0.000 description 14
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 13
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 13
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 13
- ZMCUDHNSHCRDBT-UHFFFAOYSA-M caesium bicarbonate Chemical compound [Cs+].OC([O-])=O ZMCUDHNSHCRDBT-UHFFFAOYSA-M 0.000 description 13
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 13
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 13
- 229910052808 lithium carbonate Inorganic materials 0.000 description 13
- 229910000032 lithium hydrogen carbonate Inorganic materials 0.000 description 13
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 13
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 13
- 235000015497 potassium bicarbonate Nutrition 0.000 description 13
- 239000011736 potassium bicarbonate Substances 0.000 description 13
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 13
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 13
- 229910000029 sodium carbonate Inorganic materials 0.000 description 13
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 13
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 11
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 10
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 10
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 10
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 235000013311 vegetables Nutrition 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 229910052727 yttrium Inorganic materials 0.000 description 8
- DRENHOMDLNJDOG-UHFFFAOYSA-N 2-(4-chlorophenyl)-1h-pyrazol-5-one Chemical compound C1=CC(Cl)=CC=C1N1NC(=O)C=C1 DRENHOMDLNJDOG-UHFFFAOYSA-N 0.000 description 7
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 7
- 241000238876 Acari Species 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 206010039509 Scab Diseases 0.000 description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 7
- 150000008046 alkali metal hydrides Chemical class 0.000 description 7
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 7
- 229910000105 potassium hydride Inorganic materials 0.000 description 7
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 7
- 239000012312 sodium hydride Substances 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
- 241000254173 Coleoptera Species 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 6
- 125000001246 bromo group Chemical group Br* 0.000 description 6
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 229910000103 lithium hydride Inorganic materials 0.000 description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- 235000009518 sodium iodide Nutrition 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 206010027146 Melanoderma Diseases 0.000 description 5
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- 241000244206 Nematoda Species 0.000 description 5
- KYIKRXIYLAGAKQ-UHFFFAOYSA-N abcn Chemical compound C1CCCCC1(C#N)N=NC1(C#N)CCCCC1 KYIKRXIYLAGAKQ-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229910001508 alkali metal halide Inorganic materials 0.000 description 5
- 150000008045 alkali metal halides Chemical class 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
- 239000011698 potassium fluoride Substances 0.000 description 5
- 235000003270 potassium fluoride Nutrition 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000011775 sodium fluoride Substances 0.000 description 5
- 235000013024 sodium fluoride Nutrition 0.000 description 5
- 235000010288 sodium nitrite Nutrition 0.000 description 5
- 125000003944 tolyl group Chemical group 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- DEOWCFMGCQNWDK-UHFFFAOYSA-N 4-(4-bromophenyl)-3h-1,3-thiazol-2-one Chemical compound C1=CC(Br)=CC=C1C1=CSC(=O)N1 DEOWCFMGCQNWDK-UHFFFAOYSA-N 0.000 description 4
- IDTPFOBLPOWTKL-UHFFFAOYSA-N 4-(5-chloro-1,4-dimethylpyrazol-3-yl)-2-methylphenol Chemical compound Cc1c(Cl)n(C)nc1-c1ccc(O)c(C)c1 IDTPFOBLPOWTKL-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 235000007164 Oryza sativa Nutrition 0.000 description 4
- 241000233679 Peronosporaceae Species 0.000 description 4
- 241000576755 Sclerotia Species 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 101150032964 pyr3 gene Proteins 0.000 description 4
- 235000009566 rice Nutrition 0.000 description 4
- 102200024044 rs1555523872 Human genes 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 3
- XKCRLPOFOMUDSF-UHFFFAOYSA-N 2-(2-methoxyphenyl)-1h-pyrazol-5-one Chemical compound COC1=CC=CC=C1N1NC(=O)C=C1 XKCRLPOFOMUDSF-UHFFFAOYSA-N 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- WYZDBGRXFJSYSH-UHFFFAOYSA-N 3-methoxyprop-2-enoic acid pyrrolidine-2,5-dione Chemical compound COC=CC(O)=O.O=C1CCC(=O)N1 WYZDBGRXFJSYSH-UHFFFAOYSA-N 0.000 description 3
- NJUPISSXOJDAHF-UHFFFAOYSA-N 4-(1-adamantyl)-3h-1,3-thiazol-2-one Chemical compound S1C(=O)NC(C23CC4CC(CC(C4)C2)C3)=C1 NJUPISSXOJDAHF-UHFFFAOYSA-N 0.000 description 3
- XODFWCAVOQHJFC-UHFFFAOYSA-N 4-(4-chlorophenyl)-3h-1,3-thiazol-2-one Chemical compound C1=CC(Cl)=CC=C1C1=CSC(=O)N1 XODFWCAVOQHJFC-UHFFFAOYSA-N 0.000 description 3
- VDFFNDUNESKYCU-UHFFFAOYSA-N 4-(4-fluorophenyl)-3h-1,3-thiazol-2-one Chemical compound C1=CC(F)=CC=C1C1=CSC(=O)N1 VDFFNDUNESKYCU-UHFFFAOYSA-N 0.000 description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 3
- 125000006043 5-hexenyl group Chemical group 0.000 description 3
- 241000234282 Allium Species 0.000 description 3
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 3
- 240000002791 Brassica napus Species 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 241001609607 Delia platura Species 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 244000307700 Fragaria vesca Species 0.000 description 3
- 235000016623 Fragaria vesca Nutrition 0.000 description 3
- 235000011363 Fragaria x ananassa Nutrition 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000358422 Nephotettix cincticeps Species 0.000 description 3
- 241000237502 Ostreidae Species 0.000 description 3
- 235000006040 Prunus persica var persica Nutrition 0.000 description 3
- 241000220324 Pyrus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241001414989 Thysanoptera Species 0.000 description 3
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229910000318 alkali metal phosphate Inorganic materials 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 239000002168 alkylating agent Substances 0.000 description 3
- 229940100198 alkylating agent Drugs 0.000 description 3
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 235000020971 citrus fruits Nutrition 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 3
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 3
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 3
- PWZUZQNZVZKCBI-UHFFFAOYSA-N o-ethyl carbamothioate Chemical compound CCOC(N)=S PWZUZQNZVZKCBI-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 235000020636 oyster Nutrition 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 3
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
- 229960003975 potassium Drugs 0.000 description 3
- 239000011591 potassium Chemical group 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 2
- LQXIVMYOLYCNMZ-UHFFFAOYSA-N 1,3-dimethylpyrazole-4-carbonyl chloride Chemical compound CC1=NN(C)C=C1C(Cl)=O LQXIVMYOLYCNMZ-UHFFFAOYSA-N 0.000 description 2
- GTXIUQFVBGZSJJ-UHFFFAOYSA-N 1,5-dimethylpyrazole-4-carbonyl chloride Chemical compound CC1=C(C(Cl)=O)C=NN1C GTXIUQFVBGZSJJ-UHFFFAOYSA-N 0.000 description 2
- WXRHFRAAEBAYNX-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-2h-tetrazol-5-one Chemical compound CC1=NN(C)C=C1N1C(=O)NN=N1 WXRHFRAAEBAYNX-UHFFFAOYSA-N 0.000 description 2
- BRPMFJUCQSGBSH-UHFFFAOYSA-N 1-(1,5-dimethylpyrazol-4-yl)-2h-tetrazol-5-one Chemical compound C1=NN(C)C(C)=C1N1C(=O)NN=N1 BRPMFJUCQSGBSH-UHFFFAOYSA-N 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 2
- MLICJRRPIIVQPM-UHFFFAOYSA-N 1-(2-methylthiophen-3-yl)-2h-tetrazol-5-one Chemical compound S1C=CC(N2C(NN=N2)=O)=C1C MLICJRRPIIVQPM-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000006017 1-propenyl group Chemical group 0.000 description 2
- HOXSSMJMPWIZJC-UHFFFAOYSA-N 1-tert-butyl-5-methylpyrazole-4-carbonyl chloride Chemical compound C(C)(C)(C)N1N=CC(=C1C)C(=O)Cl HOXSSMJMPWIZJC-UHFFFAOYSA-N 0.000 description 2
- 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 2
- 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 2
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 2
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 description 2
- 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 2
- 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 2
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 2
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 2
- UYBSZBKNIIWFMV-UHFFFAOYSA-N 2-methylpyridine-3-carbonyl chloride Chemical compound CC1=NC=CC=C1C(Cl)=O UYBSZBKNIIWFMV-UHFFFAOYSA-N 0.000 description 2
- ARFSLZDAEPADKY-UHFFFAOYSA-N 2-methylthiophene-3-carbonyl chloride Chemical compound CC=1SC=CC=1C(Cl)=O ARFSLZDAEPADKY-UHFFFAOYSA-N 0.000 description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- FRYGURCEQLOJIA-UHFFFAOYSA-N 4-(1-tert-butyl-5-methylpyrazol-4-yl)-1H-tetrazol-5-one Chemical compound C(C)(C)(C)N1N=CC(=C1C)N1N=NNC1=O FRYGURCEQLOJIA-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 240000002234 Allium sativum Species 0.000 description 2
- 241000213004 Alternaria solani Species 0.000 description 2
- 241000256186 Anopheles <genus> Species 0.000 description 2
- 241001279740 Anopheles sinensis Species 0.000 description 2
- 241000254175 Anthonomus grandis Species 0.000 description 2
- 241001600408 Aphis gossypii Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 235000011299 Brassica oleracea var botrytis Nutrition 0.000 description 2
- 240000003259 Brassica oleracea var. botrytis Species 0.000 description 2
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 2
- 235000002566 Capsicum Nutrition 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 241000207199 Citrus Species 0.000 description 2
- 241001133184 Colletotrichum agaves Species 0.000 description 2
- 235000017788 Cydonia oblonga Nutrition 0.000 description 2
- 241000221787 Erysiphe Species 0.000 description 2
- PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000654868 Frankliniella fusca Species 0.000 description 2
- 241000927584 Frankliniella occidentalis Species 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 241001181532 Hemileia vastatrix Species 0.000 description 2
- 241001299253 Henosepilachna vigintioctopunctata Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241001470017 Laodelphax striatella Species 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- 241000966204 Lissorhoptrus oryzophilus Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 244000070406 Malus silvestris Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000257159 Musca domestica Species 0.000 description 2
- 241000721621 Myzus persicae Species 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 241001556089 Nilaparvata lugens Species 0.000 description 2
- 235000004347 Perilla Nutrition 0.000 description 2
- 244000124853 Perilla frutescens Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 241001674048 Phthiraptera Species 0.000 description 2
- 241001439019 Phthorimaea operculella Species 0.000 description 2
- 241000758706 Piperaceae Species 0.000 description 2
- 241000595629 Plodia interpunctella Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Chemical class 0.000 description 2
- 241000254101 Popillia japonica Species 0.000 description 2
- 240000005809 Prunus persica Species 0.000 description 2
- 241000221301 Puccinia graminis Species 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 244000184734 Pyrus japonica Species 0.000 description 2
- 244000088415 Raphanus sativus Species 0.000 description 2
- 235000006140 Raphanus sativus var sativus Nutrition 0.000 description 2
- 241001481703 Rhipicephalus <genus> Species 0.000 description 2
- 241000813090 Rhizoctonia solani Species 0.000 description 2
- 241000365764 Scirtothrips dorsalis Species 0.000 description 2
- 241000221662 Sclerotinia Species 0.000 description 2
- 235000003434 Sesamum indicum Nutrition 0.000 description 2
- 244000040738 Sesamum orientale Species 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 240000003829 Sorghum propinquum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 241000339374 Thrips tabaci Species 0.000 description 2
- 241000333690 Tineola bisselliella Species 0.000 description 2
- 241000368303 Unaspis citri Species 0.000 description 2
- 244000078534 Vaccinium myrtillus Species 0.000 description 2
- 241000317942 Venturia <ichneumonid wasp> Species 0.000 description 2
- 235000009754 Vitis X bourquina Nutrition 0.000 description 2
- 235000012333 Vitis X labruscana Nutrition 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001540 azides Chemical class 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 2
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 230000009969 flowable effect Effects 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 235000004611 garlic Nutrition 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229940071870 hydroiodic acid Drugs 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 2
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- 229940102396 methyl bromide Drugs 0.000 description 2
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical compound COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- 125000005246 nonafluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 2
- 239000002420 orchard Substances 0.000 description 2
- JAZLVNXWYDFQFE-UHFFFAOYSA-N oxalyl dibromide Chemical compound BrC(=O)C(Br)=O JAZLVNXWYDFQFE-UHFFFAOYSA-N 0.000 description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 235000021017 pears Nutrition 0.000 description 2
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- PZHNNJXWQYFUTD-UHFFFAOYSA-N phosphorus triiodide Chemical compound IP(I)I PZHNNJXWQYFUTD-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 description 2
- 125000003226 pyrazolyl group Chemical group 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 102220065736 rs543286136 Human genes 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000005920 sec-butoxy group Chemical group 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 229910052714 tellurium Inorganic materials 0.000 description 2
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 description 2
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 2
- 229950011008 tetrachloroethylene Drugs 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 125000004149 thio group Chemical group *S* 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 2
- ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical compound CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 description 1
- 125000006765 (C2-C6) haloalkenyloxy group Chemical group 0.000 description 1
- 125000006767 (C2-C6) haloalkynyloxy group Chemical group 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- CRCTZWNJRMZUIO-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical group FC(F)(F)[CH]C(F)(F)F CRCTZWNJRMZUIO-UHFFFAOYSA-N 0.000 description 1
- RMHCWMIZBMGHKV-UHFFFAOYSA-N 1,1,2,3,3,4,4,5,5,6,6,6-dodecafluorohex-1-ene Chemical compound FC(F)=C(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F RMHCWMIZBMGHKV-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZAIDIVBQUMFXEC-UHFFFAOYSA-N 1,1-dichloroprop-1-ene Chemical group CC=C(Cl)Cl ZAIDIVBQUMFXEC-UHFFFAOYSA-N 0.000 description 1
- VMFCTZUYOILUMY-UHFFFAOYSA-N 1,1-difluoro-2-iodoethane Chemical compound FC(F)CI VMFCTZUYOILUMY-UHFFFAOYSA-N 0.000 description 1
- 125000006033 1,1-dimethyl-2-propenyl group Chemical group 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical compound FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
- GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 description 1
- 125000006035 1,2-dimethyl-2-propenyl group Chemical group 0.000 description 1
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- YALJPBXSARRWTA-UHFFFAOYSA-N 1,3-dimethylpyrazole-4-carboxylic acid Chemical compound CC1=NN(C)C=C1C(O)=O YALJPBXSARRWTA-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- SKTIXLZNJZTGRT-UHFFFAOYSA-N 1,5-dimethylpyrazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C=NN1C SKTIXLZNJZTGRT-UHFFFAOYSA-N 0.000 description 1
- PUMGSAJIASBPQN-UHFFFAOYSA-N 1-(1,3-dimethylpyrazol-4-yl)-4-methyltetrazol-5-one Chemical compound CN1N=C(C(=C1)N1N=NN(C1=O)C)C PUMGSAJIASBPQN-UHFFFAOYSA-N 0.000 description 1
- BLGVQSKFMBNNNE-UHFFFAOYSA-N 1-(1,5-dimethylpyrazol-4-yl)-4-methyltetrazol-5-one Chemical compound CN1N=CC(=C1C)N1N=NN(C1=O)C BLGVQSKFMBNNNE-UHFFFAOYSA-N 0.000 description 1
- BKGDCFYBXFVLFX-UHFFFAOYSA-N 1-(1-tert-butyl-5-methylpyrazol-4-yl)-4-methyltetrazol-5-one Chemical compound C(C)(C)(C)N1N=CC(=C1C)N1N=NN(C1=O)C BKGDCFYBXFVLFX-UHFFFAOYSA-N 0.000 description 1
- MFCQXMXPVBQBSP-UHFFFAOYSA-N 1-(2-methylpyridin-3-yl)-2h-tetrazol-5-one Chemical compound CC1=NC=CC=C1N1C(=O)NN=N1 MFCQXMXPVBQBSP-UHFFFAOYSA-N 0.000 description 1
- BTDAUZLVABMUJM-UHFFFAOYSA-N 1-(4-methoxy-3-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(OC)C(C)=C1 BTDAUZLVABMUJM-UHFFFAOYSA-N 0.000 description 1
- JDYBJGIGEMJCRU-UHFFFAOYSA-N 1-[2-(bromomethyl)pyridin-3-yl]-4-methyltetrazol-5-one Chemical compound BrCC1=NC=CC=C1N1N=NN(C1=O)C JDYBJGIGEMJCRU-UHFFFAOYSA-N 0.000 description 1
- JTYWFRSOTQWQNP-UHFFFAOYSA-N 1-[2-(bromomethyl)thiophen-3-yl]-4-methyltetrazol-5-one Chemical compound BrCC=1SC=CC=1N1N=NN(C1=O)C JTYWFRSOTQWQNP-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- VCEFJEPCDSVYLZ-UHFFFAOYSA-N 1-[3-(bromomethyl)-1-methylpyrazol-4-yl]-4-methyltetrazol-5-one Chemical compound CN1N=C(C(=C1)N1N=NN(C1=O)C)CBr VCEFJEPCDSVYLZ-UHFFFAOYSA-N 0.000 description 1
- BCMCDKJQCUMSKC-UHFFFAOYSA-N 1-[3-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-1-methylpyrazol-4-yl]-4-methyltetrazol-5-one Chemical compound CN1N=C(C(=C1)N1N=NN(C1=O)C)COC1=NN(C=C1)C1=CC=C(C=C1)Cl BCMCDKJQCUMSKC-UHFFFAOYSA-N 0.000 description 1
- NDAWZJRULMFMET-UHFFFAOYSA-N 1-[5-(bromomethyl)-1-methylpyrazol-4-yl]-4-methyltetrazol-5-one Chemical compound CN1N=CC(=C1CBr)N1N=NN(C1=O)C NDAWZJRULMFMET-UHFFFAOYSA-N 0.000 description 1
- PRTHZVVHFDWBOH-UHFFFAOYSA-N 1-[5-(bromomethyl)-1-tert-butylpyrazol-4-yl]-4-methyltetrazol-5-one Chemical compound C(C)(C)(C)N1N=CC(=C1CBr)N1N=NN(C1=O)C PRTHZVVHFDWBOH-UHFFFAOYSA-N 0.000 description 1
- QCNGXVSWWKPMQV-UHFFFAOYSA-N 1-[5-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-1-methylpyrazol-4-yl]-4-methyltetrazol-5-one Chemical compound CN1N=CC(=C1COC1=NN(C=C1)C1=CC=C(C=C1)Cl)N1N=NN(C1=O)C QCNGXVSWWKPMQV-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- ZJEQUGWMBSKCCM-UHFFFAOYSA-N 1-bromopiperidine-2,6-dione Chemical compound BrN1C(=O)CCCC1=O ZJEQUGWMBSKCCM-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- ADFIFDHDLIZVFW-UHFFFAOYSA-N 1-chloropiperidine-2,6-dione Chemical compound ClN1C(=O)CCCC1=O ADFIFDHDLIZVFW-UHFFFAOYSA-N 0.000 description 1
- 125000006037 1-ethyl-2-propenyl group Chemical group 0.000 description 1
- 125000006039 1-hexenyl group Chemical group 0.000 description 1
- 125000006025 1-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006019 1-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006028 1-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006021 1-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006030 1-methyl-3-butenyl group Chemical group 0.000 description 1
- SUEZECDTAQAZHA-UHFFFAOYSA-N 1-methyl-4-(2-methylpyridin-3-yl)tetrazol-5-one Chemical compound CC1=NC=CC=C1N1N=NN(C1=O)C SUEZECDTAQAZHA-UHFFFAOYSA-N 0.000 description 1
- YLQMUCPUMRVSDJ-UHFFFAOYSA-N 1-methyl-4-(2-methylthiophen-3-yl)tetrazol-5-one Chemical compound CC=1SC=CC=1N1N=NN(C1=O)C YLQMUCPUMRVSDJ-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- OTFVOPYELVXHGT-UHFFFAOYSA-N 1-tert-butyl-5-methylpyrazole-4-carboxylic acid Chemical compound CC1=C(C(O)=O)C=NN1C(C)(C)C OTFVOPYELVXHGT-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 1
- MARXMDRWROUXMD-UHFFFAOYSA-N 2-bromoisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(Br)C(=O)C2=C1 MARXMDRWROUXMD-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000000042 2-butynylthio group Chemical group [H]C([H])([H])C#CC([H])([H])S* 0.000 description 1
- AZYGEWXDKHFOKB-UHFFFAOYSA-N 2-chloro-1,3,2-benzodioxaborole Chemical compound C1=CC=C2OB(Cl)OC2=C1 AZYGEWXDKHFOKB-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- 125000006029 2-methyl-2-butenyl group Chemical group 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000006031 2-methyl-3-butenyl group Chemical group 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- 125000006101 2-methylbutyl sulfinyl group Chemical group 0.000 description 1
- 125000006131 2-methylbutyl sulfonyl group Chemical group 0.000 description 1
- 125000004714 2-methylbutylthio group Chemical group CC(CS*)CC 0.000 description 1
- HNTZKNJGAFJMHQ-UHFFFAOYSA-N 2-methylpyridine-3-carboxylic acid Chemical compound CC1=NC=CC=C1C(O)=O HNTZKNJGAFJMHQ-UHFFFAOYSA-N 0.000 description 1
- YJZOPBSZDIBXBG-UHFFFAOYSA-N 2-methylthiophene-3-carboxylic acid Chemical compound CC=1SC=CC=1C(O)=O YJZOPBSZDIBXBG-UHFFFAOYSA-N 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- 125000006024 2-pentenyl group Chemical group 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- IMOYOUMVYICGCA-UHFFFAOYSA-N 2-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C=C1C(C)(C)C IMOYOUMVYICGCA-UHFFFAOYSA-N 0.000 description 1
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- ASZZHBXPMOVHCU-UHFFFAOYSA-N 3,9-diazaspiro[5.5]undecane-2,4-dione Chemical compound C1C(=O)NC(=O)CC11CCNCC1 ASZZHBXPMOVHCU-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- VLRGXXKFHVJQOL-UHFFFAOYSA-N 3-chloropentane-2,4-dione Chemical compound CC(=O)C(Cl)C(C)=O VLRGXXKFHVJQOL-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000006305 3-iodophenyl group Chemical group [H]C1=C([H])C(I)=C([H])C(*)=C1[H] 0.000 description 1
- HRADVHZVMOMEPU-UHFFFAOYSA-N 3-iodopyrrolidine-2,5-dione Chemical compound IC1CC(=O)NC1=O HRADVHZVMOMEPU-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000006027 3-methyl-1-butenyl group Chemical group 0.000 description 1
- 125000006032 3-methyl-3-butenyl group Chemical group 0.000 description 1
- 125000006110 3-methylpentyl sulfinyl group Chemical group 0.000 description 1
- 125000005925 3-methylpentyloxy group Chemical group 0.000 description 1
- 125000004723 3-methylpentylthio group Chemical group CC(CCS*)CC 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- 125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DNMUMZLKDOZMEY-UHFFFAOYSA-N 4-methoxy-3-methylbenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C DNMUMZLKDOZMEY-UHFFFAOYSA-N 0.000 description 1
- 125000000439 4-methylpentoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000006111 4-methylpentyl sulfinyl group Chemical group 0.000 description 1
- 125000006141 4-methylpentyl sulfonyl group Chemical group 0.000 description 1
- 125000004724 4-methylpentylthio group Chemical group CC(CCCS*)C 0.000 description 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- XQMVBICWFFHDNN-UHFFFAOYSA-N 5-amino-4-chloro-2-phenylpyridazin-3-one;(2-ethoxy-3,3-dimethyl-2h-1-benzofuran-5-yl) methanesulfonate Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1.C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 XQMVBICWFFHDNN-UHFFFAOYSA-N 0.000 description 1
- VJCKEEVTPDWFKI-UHFFFAOYSA-N 5-chloro-3-(4-methoxy-3-methylphenyl)-1,4-dimethylpyrazole Chemical compound COc1ccc(cc1C)-c1nn(C)c(Cl)c1C VJCKEEVTPDWFKI-UHFFFAOYSA-N 0.000 description 1
- 240000005020 Acaciella glauca Species 0.000 description 1
- 241000208140 Acer Species 0.000 description 1
- 240000004731 Acer pseudoplatanus Species 0.000 description 1
- 235000002754 Acer pseudoplatanus Nutrition 0.000 description 1
- 241001143500 Aceraceae Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000256111 Aedes <genus> Species 0.000 description 1
- 241000256173 Aedes albopictus Species 0.000 description 1
- 241001136265 Agriotes Species 0.000 description 1
- 241000993143 Agromyza Species 0.000 description 1
- 241000566547 Agrotis ipsilon Species 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241001149961 Alternaria brassicae Species 0.000 description 1
- 241000266416 Alternaria japonica Species 0.000 description 1
- 241000266341 Alternaria macrospora Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000238679 Amblyomma Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- 244000144730 Amygdalus persica Species 0.000 description 1
- 244000226021 Anacardium occidentale Species 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- 241001237431 Anomala Species 0.000 description 1
- 241001414828 Aonidiella aurantii Species 0.000 description 1
- 241000172143 Aphanomyces cochlioides Species 0.000 description 1
- 241000294569 Aphelenchoides Species 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 235000011330 Armoracia rusticana Nutrition 0.000 description 1
- 240000003291 Armoracia rusticana Species 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
- 244000003416 Asparagus officinalis Species 0.000 description 1
- 235000005340 Asparagus officinalis Nutrition 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 241001503477 Athalia rosae Species 0.000 description 1
- 241000902805 Aulacophora Species 0.000 description 1
- 241001166626 Aulacorthum solani Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- 244000075850 Avena orientalis Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 241000254123 Bemisia Species 0.000 description 1
- 241001302798 Bemisia argentifolii Species 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 235000018185 Betula X alpestris Nutrition 0.000 description 1
- 235000018212 Betula X uliginosa Nutrition 0.000 description 1
- 241001450781 Bipolaris oryzae Species 0.000 description 1
- 241000238662 Blatta orientalis Species 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241001674044 Blattodea Species 0.000 description 1
- 241000994678 Botryotinia squamosa Species 0.000 description 1
- 241001465180 Botrytis Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 241000219198 Brassica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000011293 Brassica napus Nutrition 0.000 description 1
- 240000007124 Brassica oleracea Species 0.000 description 1
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000017647 Brassica oleracea var italica Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 235000010149 Brassica rapa subsp chinensis Nutrition 0.000 description 1
- 235000000536 Brassica rapa subsp pekinensis Nutrition 0.000 description 1
- 235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 1
- 241000499436 Brassica rapa subsp. pekinensis Species 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- CKVVJLSUPMRAEF-UHFFFAOYSA-N CC(C)(C)N1C(=CC=N1)COC2=NN(C=C2)C3=CC=CC=C3OC Chemical compound CC(C)(C)N1C(=CC=N1)COC2=NN(C=C2)C3=CC=CC=C3OC CKVVJLSUPMRAEF-UHFFFAOYSA-N 0.000 description 1
- AQQSEYBBVZNFDR-UHFFFAOYSA-N CC1=C(C=CC(=C1)C2=NN(C(=C2C)Cl)C)OCC3=CC=CC=N3 Chemical compound CC1=C(C=CC(=C1)C2=NN(C(=C2C)Cl)C)OCC3=CC=CC=N3 AQQSEYBBVZNFDR-UHFFFAOYSA-N 0.000 description 1
- WBUBWTUQHBAADK-UHFFFAOYSA-N COc1ccc(cc1C)-c1nn(C)c(O)c1C Chemical compound COc1ccc(cc1C)-c1nn(C)c(O)c1C WBUBWTUQHBAADK-UHFFFAOYSA-N 0.000 description 1
- 241001313742 Callosobruchus chinensis Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 240000004160 Capsicum annuum Species 0.000 description 1
- 235000008534 Capsicum annuum var annuum Nutrition 0.000 description 1
- 235000007862 Capsicum baccatum Nutrition 0.000 description 1
- 235000014036 Castanea Nutrition 0.000 description 1
- 241001070941 Castanea Species 0.000 description 1
- 241001107116 Castanospermum australe Species 0.000 description 1
- 235000010005 Catalpa ovata Nutrition 0.000 description 1
- 240000004528 Catalpa ovata Species 0.000 description 1
- 241000255579 Ceratitis capitata Species 0.000 description 1
- 241001157813 Cercospora Species 0.000 description 1
- 241000113401 Cercospora sojina Species 0.000 description 1
- 241000947067 Cercospora zeae-maydis Species 0.000 description 1
- 235000021538 Chard Nutrition 0.000 description 1
- 241001279148 Cheyletus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 241001374606 Chlorops oryzae Species 0.000 description 1
- 241001124134 Chrysomelidae Species 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 244000241235 Citrullus lanatus Species 0.000 description 1
- 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 241000555678 Citrus unshiu Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 241000098289 Cnaphalocrocis medinalis Species 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 240000007154 Coffea arabica Species 0.000 description 1
- 241000222199 Colletotrichum Species 0.000 description 1
- 241001429695 Colletotrichum graminicola Species 0.000 description 1
- 241000998302 Colletotrichum tabaci Species 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- 244000205754 Colocasia esculenta Species 0.000 description 1
- 240000004270 Colocasia esculenta var. antiquorum Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 240000006766 Cornus mas Species 0.000 description 1
- 235000001543 Corylus americana Nutrition 0.000 description 1
- 240000007582 Corylus avellana Species 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- 241000609458 Corynespora Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 241000258922 Ctenocephalides Species 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- 241000219130 Cucurbita pepo subsp. pepo Species 0.000 description 1
- 235000003954 Cucurbita pepo var melopepo Nutrition 0.000 description 1
- 241000219104 Cucurbitaceae Species 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- 241000144210 Culex pipiens pallens Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241001635274 Cydia pomonella Species 0.000 description 1
- 244000019459 Cynara cardunculus Species 0.000 description 1
- 235000019106 Cynara scolymus Nutrition 0.000 description 1
- 241001345881 Cytospora sacculus Species 0.000 description 1
- 241000268912 Damalinia Species 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- 241000084475 Delia antiqua Species 0.000 description 1
- 241001128004 Demodex Species 0.000 description 1
- 241001481695 Dermanyssus gallinae Species 0.000 description 1
- 241000238710 Dermatophagoides Species 0.000 description 1
- 241000489975 Diabrotica Species 0.000 description 1
- 241001508802 Diaporthe Species 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 description 1
- 235000002723 Dioscorea alata Nutrition 0.000 description 1
- 235000007056 Dioscorea composita Nutrition 0.000 description 1
- 235000009723 Dioscorea convolvulacea Nutrition 0.000 description 1
- 235000005362 Dioscorea floribunda Nutrition 0.000 description 1
- 235000004868 Dioscorea macrostachya Nutrition 0.000 description 1
- 235000005361 Dioscorea nummularia Nutrition 0.000 description 1
- 235000005360 Dioscorea spiculiflora Nutrition 0.000 description 1
- 241000663351 Diplocarpon rosae Species 0.000 description 1
- 241001517923 Douglasiidae Species 0.000 description 1
- 241001183635 Echinocnemus Species 0.000 description 1
- 241000901048 Elsinoe ampelina Species 0.000 description 1
- 241001568757 Elsinoe glycines Species 0.000 description 1
- 241001564064 Elsinoe theae Species 0.000 description 1
- 235000009008 Eriobotrya japonica Nutrition 0.000 description 1
- 244000061508 Eriobotrya japonica Species 0.000 description 1
- 244000004281 Eucalyptus maculata Species 0.000 description 1
- 241001539473 Euphoria Species 0.000 description 1
- 206010015535 Euphoric mood Diseases 0.000 description 1
- 241001411323 Exobasidium reticulatum Species 0.000 description 1
- 241000306559 Exserohilum Species 0.000 description 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- 235000009419 Fagopyrum esculentum Nutrition 0.000 description 1
- 240000008620 Fagopyrum esculentum Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000365767 Frankliniella intonsa Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241000122692 Fusarium avenaceum Species 0.000 description 1
- 241000223194 Fusarium culmorum Species 0.000 description 1
- 241000221778 Fusarium fujikuroi Species 0.000 description 1
- 241000223195 Fusarium graminearum Species 0.000 description 1
- 241000223221 Fusarium oxysporum Species 0.000 description 1
- 241001660203 Gasterophilus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000011201 Ginkgo Nutrition 0.000 description 1
- 235000008100 Ginkgo biloba Nutrition 0.000 description 1
- 244000194101 Ginkgo biloba Species 0.000 description 1
- 241000223247 Gloeocercospora Species 0.000 description 1
- 241000461774 Gloeosporium Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 241000785585 Gryllotalpa africana Species 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 241001480796 Haemaphysalis Species 0.000 description 1
- 241000257224 Haematobia Species 0.000 description 1
- 241000790933 Haematopinus Species 0.000 description 1
- 241000243976 Haemonchus Species 0.000 description 1
- 241000243974 Haemonchus contortus Species 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
- 241000825556 Halyomorpha halys Species 0.000 description 1
- 241000730161 Haritalodes derogata Species 0.000 description 1
- 244000020551 Helianthus annuus Species 0.000 description 1
- 235000003222 Helianthus annuus Nutrition 0.000 description 1
- 241001581044 Hellula undalis Species 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 241000498254 Heterodera glycines Species 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000549404 Hyaloperonospora parasitica Species 0.000 description 1
- 241000011100 Hydrelia Species 0.000 description 1
- 241001464384 Hymenolepis nana Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241000257176 Hypoderma <fly> Species 0.000 description 1
- 244000017020 Ipomoea batatas Species 0.000 description 1
- 235000002678 Ipomoea batatas Nutrition 0.000 description 1
- 235000006350 Ipomoea batatas var. batatas Nutrition 0.000 description 1
- 241000238681 Ixodes Species 0.000 description 1
- 241000238703 Ixodes scapularis Species 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 241000222058 Kabatiella Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000003228 Lactuca sativa Nutrition 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 241001177117 Lasioderma serricorne Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 241000270322 Lepidosauria Species 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 241000234280 Liliaceae Species 0.000 description 1
- 241001113970 Linognathus Species 0.000 description 1
- 241000254022 Locusta migratoria Species 0.000 description 1
- 244000241838 Lycium barbarum Species 0.000 description 1
- 235000015459 Lycium barbarum Nutrition 0.000 description 1
- 235000015468 Lycium chinense Nutrition 0.000 description 1
- 241001177134 Lyctus Species 0.000 description 1
- 241000501345 Lygus lineolaris Species 0.000 description 1
- 235000018330 Macadamia integrifolia Nutrition 0.000 description 1
- 235000003800 Macadamia tetraphylla Nutrition 0.000 description 1
- 240000000912 Macadamia tetraphylla Species 0.000 description 1
- 241000721714 Macrosiphum euphorbiae Species 0.000 description 1
- 241001344131 Magnaporthe grisea Species 0.000 description 1
- 244000081841 Malus domestica Species 0.000 description 1
- 241001575018 Matsumuraeses Species 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 238000006751 Mitsunobu reaction Methods 0.000 description 1
- 241001518729 Monilinia Species 0.000 description 1
- 241001363493 Monilinia mali Species 0.000 description 1
- 206010027982 Morphoea Diseases 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- 240000005561 Musa balbisiana Species 0.000 description 1
- 235000018290 Musa x paradisiaca Nutrition 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241001477928 Mythimna Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 229940126655 NDI-034858 Drugs 0.000 description 1
- 241001137880 Nematodirus battus Species 0.000 description 1
- 241000083073 Neopseudocercosporella capsellae Species 0.000 description 1
- 241000961933 Nephotettix virescens Species 0.000 description 1
- 241001671714 Nezara Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 241000290929 Nimbus Species 0.000 description 1
- 241001126259 Nippostrongylus brasiliensis Species 0.000 description 1
- 241000998584 Nuda Species 0.000 description 1
- 235000010676 Ocimum basilicum Nutrition 0.000 description 1
- 240000007926 Ocimum gratissimum Species 0.000 description 1
- 241001668536 Oculimacula yallundae Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- 241000238890 Ornithodoros moubata Species 0.000 description 1
- 241000346285 Ostrinia furnacalis Species 0.000 description 1
- 241001147398 Ostrinia nubilalis Species 0.000 description 1
- 241001570894 Oulema oryzae Species 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 241000382928 Oxya Species 0.000 description 1
- 241000222291 Passalora fulva Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 241001369134 Pediasia Species 0.000 description 1
- 241001507673 Penicillium digitatum Species 0.000 description 1
- 241000320508 Pentatomidae Species 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 241000238661 Periplaneta Species 0.000 description 1
- 241000238675 Periplaneta americana Species 0.000 description 1
- 241000048273 Periplaneta japonica Species 0.000 description 1
- 244000062780 Petroselinum sativum Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 235000010659 Phoenix dactylifera Nutrition 0.000 description 1
- 244000104275 Phoenix dactylifera Species 0.000 description 1
- 241001557902 Phomopsis sp. Species 0.000 description 1
- 241000210649 Phyllosticta ampelicida Species 0.000 description 1
- 241001270527 Phyllosticta citrullina Species 0.000 description 1
- 241000437063 Phyllotreta striolata Species 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241000233622 Phytophthora infestans Species 0.000 description 1
- 241000218657 Picea Species 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000003447 Pistacia vera Nutrition 0.000 description 1
- 240000006711 Pistacia vera Species 0.000 description 1
- 240000004713 Pisum sativum Species 0.000 description 1
- 235000010582 Pisum sativum Nutrition 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241001503436 Plasmodiophora brassicae Species 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 235000006485 Platanus occidentalis Nutrition 0.000 description 1
- 241000500437 Plutella xylostella Species 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000219000 Populus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 235000009827 Prunus armeniaca Nutrition 0.000 description 1
- 244000018633 Prunus armeniaca Species 0.000 description 1
- 244000007021 Prunus avium Species 0.000 description 1
- 235000010401 Prunus avium Nutrition 0.000 description 1
- 235000005805 Prunus cerasus Nutrition 0.000 description 1
- 244000141353 Prunus domestica Species 0.000 description 1
- 235000011158 Prunus mume Nutrition 0.000 description 1
- 244000018795 Prunus mume Species 0.000 description 1
- 235000006029 Prunus persica var nucipersica Nutrition 0.000 description 1
- 244000017714 Prunus persica var. nucipersica Species 0.000 description 1
- 241001322464 Pseudocercospora fuligena Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 241000758041 Ptisana squamosa Species 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241001123559 Puccinia hordei Species 0.000 description 1
- 241001123567 Puccinia sorghi Species 0.000 description 1
- 241001123583 Puccinia striiformis Species 0.000 description 1
- 241000228454 Pyrenophora graminea Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 235000001630 Pyrus pyrifolia var culta Nutrition 0.000 description 1
- 244000079529 Pyrus serotina Species 0.000 description 1
- 241001385948 Pythium sp. Species 0.000 description 1
- 241000219492 Quercus Species 0.000 description 1
- 241000173767 Ramularia Species 0.000 description 1
- 241000173769 Ramularia collo-cygni Species 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 241001361634 Rhizoctonia Species 0.000 description 1
- 241000125167 Rhopalosiphum padi Species 0.000 description 1
- 241000133710 Riptortus Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 235000017848 Rubus fruticosus Nutrition 0.000 description 1
- 240000007651 Rubus glaucus Species 0.000 description 1
- 235000011034 Rubus glaucus Nutrition 0.000 description 1
- 235000009122 Rubus idaeus Nutrition 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 0.000 description 1
- 241000509416 Sarcoptes Species 0.000 description 1
- 241001249129 Scirpophaga incertulas Species 0.000 description 1
- 241001518640 Sclerotinia homoeocarpa Species 0.000 description 1
- 241000209056 Secale Species 0.000 description 1
- 235000007238 Secale cereale Nutrition 0.000 description 1
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 1
- 241001533598 Septoria Species 0.000 description 1
- 241001597349 Septoria glycines Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 241000254152 Sitophilus oryzae Species 0.000 description 1
- 241000753145 Sitotroga cerealella Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 241000176086 Sogatella furcifera Species 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- 244000061458 Solanum melongena Species 0.000 description 1
- 206010064127 Solar lentigo Diseases 0.000 description 1
- 241001492664 Solenopsis <angiosperm> Species 0.000 description 1
- 241000517830 Solenopsis geminata Species 0.000 description 1
- 241001051088 Sphaerotheca humuli Species 0.000 description 1
- 241000532887 Sphenophorus venatus Species 0.000 description 1
- 235000009337 Spinacia oleracea Nutrition 0.000 description 1
- 244000300264 Spinacia oleracea Species 0.000 description 1
- 241000256247 Spodoptera exigua Species 0.000 description 1
- 241000985245 Spodoptera litura Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 241000255628 Tabanidae Species 0.000 description 1
- 241000255626 Tabanus <genus> Species 0.000 description 1
- 241001116498 Taxus baccata Species 0.000 description 1
- 241000191771 Teladorsagia circumcincta Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241000339373 Thrips palmi Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 241000722096 Tilletia controversa Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241000546225 Tomicus Species 0.000 description 1
- 241001271990 Tomicus piniperda Species 0.000 description 1
- 241000255901 Tortricidae Species 0.000 description 1
- 241000271862 Toxoptera Species 0.000 description 1
- 241001414833 Triatoma Species 0.000 description 1
- 241000243777 Trichinella spiralis Species 0.000 description 1
- 206010044608 Trichiniasis Diseases 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 241000122945 Trichostrongylus axei Species 0.000 description 1
- 241000243796 Trichostrongylus colubriformis Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 240000003021 Tsuga heterophylla Species 0.000 description 1
- 241000722921 Tulipa gesneriana Species 0.000 description 1
- 241000051572 Typhula sp. Species 0.000 description 1
- 241000233791 Ustilago tritici Species 0.000 description 1
- 235000003095 Vaccinium corymbosum Nutrition 0.000 description 1
- 240000001717 Vaccinium macrocarpon Species 0.000 description 1
- 235000012545 Vaccinium macrocarpon Nutrition 0.000 description 1
- 235000017537 Vaccinium myrtillus Nutrition 0.000 description 1
- 235000002118 Vaccinium oxycoccus Nutrition 0.000 description 1
- 241001669640 Venturia carpophila Species 0.000 description 1
- 241001006642 Venturia pyrina Species 0.000 description 1
- 241000082085 Verticillium <Phyllachorales> Species 0.000 description 1
- 241000190021 Zelkova Species 0.000 description 1
- 241001136529 Zeugodacus cucurbitae Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 241000981595 Zoysia japonica Species 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- QEZHSXDSWBLPKD-UHFFFAOYSA-M [Br-].CC[Mg+].C1CCOC1 Chemical compound [Br-].CC[Mg+].C1CCOC1 QEZHSXDSWBLPKD-UHFFFAOYSA-M 0.000 description 1
- WZSSXWGEAHFBAB-UHFFFAOYSA-N [I].C[Si](Cl)(C)C Chemical compound [I].C[Si](Cl)(C)C WZSSXWGEAHFBAB-UHFFFAOYSA-N 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000001785 acacia senegal l. willd gum Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 210000004883 areola Anatomy 0.000 description 1
- 235000016520 artichoke thistle Nutrition 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- UUXFWHMUNNXFHD-UHFFFAOYSA-N barium azide Chemical compound [Ba+2].[N-]=[N+]=[N-].[N-]=[N+]=[N-] UUXFWHMUNNXFHD-UHFFFAOYSA-N 0.000 description 1
- 125000004533 benzofuran-5-yl group Chemical group O1C=CC2=C1C=CC(=C2)* 0.000 description 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 235000021279 black bean Nutrition 0.000 description 1
- 235000013614 black pepper Nutrition 0.000 description 1
- 235000021029 blackberry Nutrition 0.000 description 1
- 235000021014 blueberries Nutrition 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- NRDQFWXVTPZZAZ-UHFFFAOYSA-N butyl carbonochloridate Chemical compound CCCCOC(Cl)=O NRDQFWXVTPZZAZ-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001728 capsicum frutescens Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 235000020226 cashew nut Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000004651 chloromethoxy group Chemical group ClCO* 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 235000016213 coffee Nutrition 0.000 description 1
- 235000013353 coffee beverage Nutrition 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 235000004634 cranberry Nutrition 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 125000000131 cyclopropyloxy group Chemical group C1(CC1)O* 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 125000004783 dichloromethoxy group Chemical group ClC(O*)Cl 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000006001 difluoroethyl group Chemical group 0.000 description 1
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
- 239000004316 dimethyl dicarbonate Substances 0.000 description 1
- 235000010300 dimethyl dicarbonate Nutrition 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 235000004879 dioscorea Nutrition 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- BVUAXNSNPJCWPI-UHFFFAOYSA-N ethyl 3-(4-methoxy-3-methylphenyl)-2-methyl-3-oxopropanoate Chemical compound CCOC(=O)C(C)C(=O)C1=CC=C(OC)C(C)=C1 BVUAXNSNPJCWPI-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- 125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 244000037671 genetically modified crops Species 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 125000003106 haloaryl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005980 hexynyl group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- HECSHXUNOVTAIJ-UHFFFAOYSA-N hydron;(2-methoxyphenyl)hydrazine;chloride Chemical compound Cl.COC1=CC=CC=C1NN HECSHXUNOVTAIJ-UHFFFAOYSA-N 0.000 description 1
- USZLCYNVCCDPLQ-UHFFFAOYSA-N hydron;n-methoxymethanamine;chloride Chemical compound Cl.CNOC USZLCYNVCCDPLQ-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000004357 indazolylamino group Chemical group N1N=C(C2=CC=CC=C12)N* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000026045 iodination Effects 0.000 description 1
- 238000006192 iodination reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000006303 iodophenyl group Chemical group 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 125000003384 isochromanyl group Chemical group C1(OCCC2=CC=CC=C12)* 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 125000005956 isoquinolyl group Chemical group 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229920005610 lignin Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- GUWHRJQTTVADPB-UHFFFAOYSA-N lithium azide Chemical compound [Li+].[N-]=[N+]=[N-] GUWHRJQTTVADPB-UHFFFAOYSA-N 0.000 description 1
- XKPJKVVZOOEMPK-UHFFFAOYSA-M lithium;formate Chemical compound [Li+].[O-]C=O XKPJKVVZOOEMPK-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001960 metal nitrate Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- LINPVWIEWJTEEJ-UHFFFAOYSA-N methyl 2-chloro-9-hydroxyfluorene-9-carboxylate Chemical compound C1=C(Cl)C=C2C(C(=O)OC)(O)C3=CC=CC=C3C2=C1 LINPVWIEWJTEEJ-UHFFFAOYSA-N 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- OQABVSJGPKOBNU-UHFFFAOYSA-N n,4-dimethoxy-n,3-dimethylbenzamide Chemical compound CON(C)C(=O)C1=CC=C(OC)C(C)=C1 OQABVSJGPKOBNU-UHFFFAOYSA-N 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- GRSBAMVBFWRBBH-UHFFFAOYSA-N o-ethyl chloromethanethioate Chemical compound CCOC(Cl)=S GRSBAMVBFWRBBH-UHFFFAOYSA-N 0.000 description 1
- HXFVUECWGARNTL-UHFFFAOYSA-N o-methyl chloromethanethioate Chemical compound COC(Cl)=S HXFVUECWGARNTL-UHFFFAOYSA-N 0.000 description 1
- KOSYAAIZOGNATQ-UHFFFAOYSA-N o-phenyl chloromethanethioate Chemical compound ClC(=S)OC1=CC=CC=C1 KOSYAAIZOGNATQ-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 235000011197 perejil Nutrition 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005005 perfluorohexyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 235000020233 pistachio Nutrition 0.000 description 1
- 235000021018 plums Nutrition 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 150000004804 polysaccharides Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- ZUPDNLCLXSWMAE-UHFFFAOYSA-N potassium;butan-2-olate Chemical compound [K+].CCC(C)[O-] ZUPDNLCLXSWMAE-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 description 1
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- QQKDTTWZXHEGAQ-UHFFFAOYSA-N propyl carbonochloridate Chemical compound CCCOC(Cl)=O QQKDTTWZXHEGAQ-UHFFFAOYSA-N 0.000 description 1
- DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000005554 pyridyloxy group Chemical group 0.000 description 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 235000003499 redwood Nutrition 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 206010039766 scrub typhus Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- BMYABONBEFTWQL-UHFFFAOYSA-M sodium 3-methoxyprop-2-enoate Chemical compound [Na+].COC=CC([O-])=O BMYABONBEFTWQL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- VSCLJRSWEGZJNY-UHFFFAOYSA-N sodium;butan-2-olate Chemical compound [Na+].CCC(C)[O-] VSCLJRSWEGZJNY-UHFFFAOYSA-N 0.000 description 1
- SUBJHSREKVAVAR-UHFFFAOYSA-N sodium;methanol;methanolate Chemical compound [Na+].OC.[O-]C SUBJHSREKVAVAR-UHFFFAOYSA-N 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- WBQTXTBONIWRGK-UHFFFAOYSA-N sodium;propan-2-olate Chemical compound [Na+].CC(C)[O-] WBQTXTBONIWRGK-UHFFFAOYSA-N 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013616 tea Nutrition 0.000 description 1
- VVKCNYOQHJEXRB-UHFFFAOYSA-N tert-butyl chloro carbonate Chemical compound CC(C)(C)OC(=O)OCl VVKCNYOQHJEXRB-UHFFFAOYSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 229940125670 thienopyridine Drugs 0.000 description 1
- 239000002175 thienopyridine Substances 0.000 description 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229940096911 trichinella spiralis Drugs 0.000 description 1
- 208000003982 trichinellosis Diseases 0.000 description 1
- 201000007588 trichinosis Diseases 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
式(1)〔式中、Eは、下記の基E16等を表し;Yは、−O−CH2−等を表し;Qは、下記の基Q46等を表し;R8は、C1−C6アルキル基等を表し;R3,R30およびR31は同一又は相異なり水素原子等を表し;Aは、群P1から選ばれる1以上の原子もしくは基を有していてもよいC6−C16アリール基等を表し;R5は、C1−C3アルキル基等を表し;Xは、酸素原子または硫黄原子を表す。〕で示されるテトラゾリノン化合物は、有害生物に対して優れた防除効力を有する。Formula (1) [In the formula, E represents the following group E16 and the like; Y represents —O—CH 2 and the like; Q represents the following group Q46 and the like; and R8 represents a C1-C6 alkyl group. R3, R30 and R31 are the same or different and each represents a hydrogen atom or the like; A represents a C6-C16 aryl group or the like which may have one or more atoms or groups selected from the group P1; R5 represents a C1-C3 alkyl group or the like; X represents an oxygen atom or a sulfur atom. ] The tetrazolinone compound shown by this has the outstanding control effect with respect to a pest.
Description
本発明はテトラゾリノン化合物及びその用途に関する。 The present invention relates to tetrazolinone compounds and uses thereof.
従来より、有害生物を防除するために種々の薬剤が開発され、実用に供されているが、これらの薬剤は必ずしも十分ではない。
一方、6員環ヘテロ環で置換されたテトラゾリノン環を有する化合物として、
下記式(A1)および(A2)
で示される化合物が知られている(EP0692482A参照。)。
また、5員環ヘテロ環で置換されたテトラゾリノン環を有する化合物として、
下記式(B1)および(B2)
で示される化合物が知られている(EP0695748A参照。)。Conventionally, various drugs have been developed and put into practical use for controlling pests, but these drugs are not always sufficient.
On the other hand, as a compound having a tetrazolinone ring substituted with a 6-membered heterocycle,
The following formulas (A1) and (A2)
Is known (see EP 0694822A).
In addition, as a compound having a tetrazolinone ring substituted with a 5-membered heterocycle,
The following formulas (B1) and (B2)
Is known (see EP0695748A).
本発明は、有害生物に対して優れた防除効力を有する化合物を提供する。 The present invention provides a compound having an excellent control effect against pests.
本発明者らは、有害生物に対して優れた防除効力を有する化合物を見出すべく検討した結果、下記式(1)で示されるテトラゾリノン化合物が有害生物に対して優れた防除効力を有することを見出し、本発明を完成した。
すなわち、本発明は以下の〔1〕〜〔6〕のとおりである。
〔1〕 式(1)
〔式中、
R5は、1以上のハロゲン原子を有していてもよいC1−C3アルキル基を表し;
Eは2価の5員ヘテロアリール基または2価の6員ヘテロアリール基を表し;
Yは、*−(CH2)n−G−&、*−G−(CH2)n−&、*−G−(CH2)n−G−&、*−G−CH2CH2−G−CH2CH2−G−&、*−CH2−G−CH2CH2−G−&、*−G−CH2CH2−G−CH2−&、*−CH=CH−&、*−CH=CH−G−&、*−G−CH=CH−&、*−CH=CH=CH2−G−&、*−G−CH2−CH=CH−&、*−G−CH=CH=CH2−&、*−CH2−CH=CH−G−&、*−CH=CH−G−CH2−&、*−CH2−G−CH=CH−&、*−CH=CH−CH2−G−CH2−&、*−CH2−G−CH2−CH=CH−&、*−CH=CH−G−CH2CH2−&、*−CH2CH2−G−CH=CH−&、*−G−CH=CH−CH2CH2−&、*−CH2CH2−CH=CH−G−&、*−CH=CH−G−CH=CH−&、*−C≡C−&、*−C≡C−CH2−G−&、*−G−CH2−C≡C−&、*−C≡C−CH2−G−CH2−&または*−CH2−G−CH2−C≡C−&を表し
(但し、Yの有する全ての水素原子は(Gが有する水素原子を含む)、ハロゲン原子およびC1−C3アルキル基からなる群より選ばれる1以上の原子または基で置換されていてもよく、2以上の原子または基で置換される場合、該原子および基は同一または相異なっていてもよく;Gは酸素原子、硫黄原子、またはNRBを表し;RBは、水素原子またはC1−C3アルキル基を表し、nは1〜10の整数を表す。また、Yにおいて、*はQとの結合位置を表し、&はEとの結合位置を表す。);
Qは、2価のC6−C10アリール基(但し、該2価のC6−C10アリール基は、群P2から選ばれる1以上の原子または基を有していてもよい。)または2価の5−10員ヘテロ環基(但し、該2価の5−10員ヘテロ環基は、群P2から選ばれる1以上の原子もしくは基を有していてもよく、環構成原子として窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を含有し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。)を表し;
Xは、酸素原子または硫黄原子を表し;
Aは、C6−C10アリール基、アダマンチル基、C6−C10アリールオキシ基、C6−C10アリールチオ基、C6−C10アリールアミノ基、C3−C10シクロアルキル基、5−10員ヘテロ環基(但し、該5−10員ヘテロ環基は、環構成原子として窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を含有し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。)、5−10員ヘテロアリールオキシ基(但し、該5−10員ヘテロアリールオキシ基は、環構成原子として窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を含有し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。)、5−10員ヘテロアリールチオ基(但し、該5−10員ヘテロアリールチオ基は、環構成原子として窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を含有し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。)、5−10員ヘテロアリールアミノ基(但し、該5−10員ヘテロアリールアミノ基は、環構成原子として窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を含有し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。)、C6−C10アリールスルホニル基、C6−C10アリールスルフィニル基、または群P3から選ばれる1もしくは2の基を有していてもよい−CH=NH(但し、該−CH=NHが群P3から選ばれる基を2つ有する場合、該基は同一または相異なっていてもよい。)を表す(但し、該C6−C10アリール基、アダマンチル基、C6−C10アリールオキシ基、C6−C10アリールチオ基、C6−C10アリールアミノ基、C3−C10シクロアルキル基、5−10員ヘテロ環基、5−10員ヘテロアリールオキシ基、5−10員ヘテロアリールチオ基、5−10員ヘテロアリールアミノ基、C6−C10アリールスルホニル基およびC6−C10アリールスルフィニル基は、群P1から選ばれる1以上の原子もしくは基を有していてもよく、2以上の原子もしくは基を有する場合、該原子もしくは基は同一または相異なっていてもよい。)。
群P1:ハロゲン原子、C1−C6アルキル基、C1−C6ハロアルキル基、C2−C6アルケニル基、C2−C6ハロアルケニル基、C2−C6アルキニル基、C2−C6ハロアルキニル基、C3−C6シクロアルキル基、C3−C6ハロシクロアルキル基、C1−C6アルコキシ基、C1−C6ハロアルコキシ基、C1−C6アルキルチオ基、C1−C6ハロアルキルチオ基、C3−C6シクロアルキルオキシ基、C3−C6ハロシクロアルキルオキシ基、C3−C6シクロアルキルチオ基、C3−C6アルケニルオキシ基、C3−C6アルキニルオキシ基、C3−C6ハロアルケニルオキシ基、C3−C6ハロアルキニルオキシ基、C3−C6アルケニルチオ基、C3−C6アルキニルチオ基、C3−C6ハロアルケニルチオ基、C3−C6ハロアルキニルチオ基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C6アルキルカルボニルオキシ基、C2−C6アルキルカルボニルチオ基、カルボキシ基、ホルミル基、C2−C6アルコキシカルボニル基、ニトロ基、シアノ基、ヒドロキシ基、C1−C6アルキルスルホニル基、C1−C6ハロアルキルスルホニル基、、C1−C6アルキルスルフィニル基、C1−C6ハロアルキルスルフィニル基、C1−C6アルキル基を有していてもよいアミノ基、C1−C6アルキル基を有していてもよいアミノスルホニル基およびC1−C6アルキル基を有していてもよいアミノカルボニル基からなる群。
群P2:ハロゲン原子、シアノ基、C3−C6シクロアルキル基、C3−C6ハロシクロアルキル基、C1−C4アルコキシ基、C1−C4ハロアルコキシ基、C1−C4アルキルチオ基およびC1−C4ハロアルキルチオ基からなる群。
群P3:C1−C6アルキル基、C1−C6ハロアルキル基、C3−C6シクロアルキル基、およびC3−C6ハロシクロアルキル基からなる群。〕
で示されるテトラゾリノン化合物。As a result of studies to find a compound having an excellent control effect against pests, the present inventors have found that the tetrazolinone compound represented by the following formula (1) has an excellent control effect against pests. The present invention has been completed.
That is, the present invention is as follows [1] to [6].
[1] Formula (1)
[Where,
R 5 represents a C1-C3 alkyl group optionally having one or more halogen atoms;
E represents a divalent 5-membered heteroaryl group or a divalent 6-membered heteroaryl group;
Y is, * - (CH 2) n -G - &, * - G- (CH 2) n - &, * - G- (CH 2) n -G - &, * - G-CH 2 CH 2 - G-CH 2 CH 2 -G - &, * - CH 2 -G-CH 2 CH 2 -G - &, * - G-CH 2 CH 2 -G-CH 2 - &, * - CH = CH- & , * - CH = CH-G - &, * - G-CH = CH - &, * - CH = CH = CH 2 -G - &, * - G-CH 2 -CH = CH - &, * - G -CH = CH = CH 2 - & , * - CH 2 -CH = CH-G - &, * - CH = CH-G-CH 2 - &, * - CH 2 -G-CH = CH - &, * -CH = CH-CH 2 -G- CH 2 - &, * - CH 2 -G-CH 2 -CH = CH - &, * - CH = CH-G-CH 2 CH 2 - &, * - CH 2 CH 2 -G-CH = CH- & * -G-CH = CH-CH 2 CH 2 - &, * - CH 2 CH 2 -CH = CH-G - &, * - CH = CH-G-CH = CH - &, * - C≡C- &, * - C≡C-CH 2 -G - &, * - G-CH 2 -C≡C - &, * - C≡C-CH 2 -G-CH 2 - & or * -CH 2 -G —CH 2 —C≡C— & (wherein all the hydrogen atoms of Y (including the hydrogen atom of G) are one or more atoms selected from the group consisting of halogen atoms and C1-C3 alkyl groups Or when substituted with two or more atoms or groups, the atoms and groups may be the same or different; G represents an oxygen atom, a sulfur atom, or NR B ; R B represents a hydrogen atom or a C1-C3 alkyl group, n represents an integer from 1 to 10. Furthermore, our in Y Te, * represents the bonding position with Q, & represents a bonding position to E).;
Q is a divalent C6-C10 aryl group (provided that the bivalent C6-C10 aryl group may have one or more atoms or groups selected from the group P 2.) Or divalent 5-10-membered heterocyclic group (provided that the divalent 5-10-membered heterocyclic group may have one or more atoms or groups selected from group P 2 , and a nitrogen atom as a ring-constituting atom, 1 or more atoms selected from the group consisting of an oxygen atom and a sulfur atom are contained, and when 2 or more atoms are contained, these atoms may be the same or different.
X represents an oxygen atom or a sulfur atom;
A represents a C6-C10 aryl group, an adamantyl group, a C6-C10 aryloxy group, a C6-C10 arylthio group, a C6-C10 arylamino group, a C3-C10 cycloalkyl group, a 5-10-membered heterocyclic group (provided that the The 5- to 10-membered heterocyclic group contains one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring-constituting atoms. 5-10 membered heteroaryloxy group (provided that the 5-10 membered heteroaryloxy group is one or more selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a ring-constituting atom) In the case where two or more atoms are contained, the atoms may be the same or different, and a 5- to 10-membered heteroarylthio group (provided that The 5- to 10-membered heteroarylthio group contains one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring constituent atoms, and when containing two or more atoms, the atoms are the same or 5-10 membered heteroarylamino group (provided that the 5-10 membered heteroarylamino group is selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a ring atom) It contains more atoms, when containing 2 or more atoms, the atoms may be different from the same or different.), selected from C6-C10 arylsulfonyl group, C6-C10 arylsulfinyl group or group P 3, good -CH = NH optionally having 1 or 2 groups that are (when the -CH = NH has two groups selected from the group P 3, the base may be the same or different Which may be different from each other. However, the C6-C10 aryl group, adamantyl group, C6-C10 aryloxy group, C6-C10 arylthio group, C6-C10 arylamino group, C3-C10 cycloalkyl group, 5 A -10 membered heterocyclic group, a 5-10 membered heteroaryloxy group, a 5-10 membered heteroarylthio group, a 5-10 membered heteroarylamino group, a C6-C10 arylsulfonyl group and a C6-C10 arylsulfinyl group are It may have one or more atoms or groups selected from P 1 , and when it has two or more atoms or groups, these atoms or groups may be the same or different.)
Group P 1 : halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 haloalkynyl group, C3-C6 cycloalkyl Group, C3-C6 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C3-C6 cycloalkyloxy group, C3-C6 halocycloalkyl group Oxy group, C3-C6 cycloalkylthio group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C3-C6 haloalkenyloxy group, C3-C6 haloalkynyloxy group, C3-C6 alkenylthio group, C3-C6 Alkynylthio group, C3-C6 haloalkenylthio group, C -C6 haloalkynylthio group, C2-C6 alkylcarbonyl group, C2-C6 haloalkylcarbonyl group, C2-C6 alkylcarbonyloxy group, C2-C6 alkylcarbonylthio group, carboxy group, formyl group, C2-C6 alkoxycarbonyl group, It may have a nitro group, a cyano group, a hydroxy group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 alkyl group. A group consisting of an amino group, an aminosulfonyl group optionally having a C1-C6 alkyl group, and an aminocarbonyl group optionally having a C1-C6 alkyl group.
Group P 2 : halogen atom, cyano group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group and C1-C4 haloalkylthio group A group consisting of
Group P 3 : A group consisting of a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, and a C3-C6 halocycloalkyl group. ]
A tetrazolinone compound represented by:
〔2〕 Eが、群P4から選ばれいずれか一の基である、〔1〕に記載のテトラゾリノン化合物。
群P4:E1〜E7からなる群。
〔式中、#はテトラゾリノン環との結合位置を表し、$はYとの結合位置を表す。また、Z1は、窒素原子またはCR1を表し;Z2は、窒素原子またはCR2を表し;Z3は、窒素原子またはCR3を表し;Z4は、窒素原子またはCR4を表し;
Y1は、酸素原子、硫黄原子またはNR8を表し;Y2は、酸素原子、硫黄原子またはNR6を表し; Y3は、酸素原子、硫黄原子またはNR7を表し;
R1は、水素原子、C1−C6アルキル基、C3−C6シクロアルキル基、ハロゲン原子、C1−C6ハロアルキル基、C2−C6アルケニル基、C1−C6アルコキシ基、C1−C6アルキルチオ基、C2−C6アルキニル基、ニトロ基、シアノ基、C1−C6アルキル基を有していてもよいアミノカルボニル基、
C2−C6ハロアルケニル基、C2−C6ハロアルキニル基、C3−C6ハロシクロアルキル基、C1−C6ハロアルコキシ基、C1−C6ハロアルキルチオ基、C3−C6シクロアルキルオキシ基、C3−C6ハロシクロアルキルオキシ基、C3−C6シクロアルキルチオ基、C3−C6アルケニルオキシ基、C3−C6アルキニルオキシ基、C3−C6ハロアルケニルオキシ基、C3−C6ハロアルキニルオキシ基、C3−C6アルケニルチオ基、C3−C6アルキニルチオ基、C3−C6ハロアルケニルチオ基、C3−C6ハロアルキニルチオ基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C6アルキルカルボニルオキシ基、C2−C6アルキルカルボニルチオ基、C2−C6アルコキシカルボニル基、ヒドロキシ基、チオール基、C1−C6アルキル基を有していてもよいアミノ基、ペンタフルオロスルファニル基、C3−C9トリアルキルシリル基、C5−C14トリアルキルシリルエチニル基、C1−C4アルキルスルホニル基、C1−C4ハロアルキルスルホニル基、C1−C4アルキルスルフィニル基、C1−C4ハロアルキルスルフィニル基、C2−C5アルコキシアルキル基またはC2−C5アルキルチオアルキル基を表し;
R2,R3およびR4はそれぞれ独立して、水素原子、ハロゲン原子、C1−C3アルキル基、C1−C3ハロアルキル基、C2−C3アルケニル基、C2−C3ハロアルケニル基またはC1−C3アルコキシ基を表し;
R6およびR7はそれぞれ独立して、水素原子、C1−C3アルキル基、C1−C3ハロアルキル基、C2−C3アルケニル基、C2−C3ハロアルケニル基またはC1−C3アルコキシ基を表し;
R8は、水素原子、C1−C6アルキル基、C3−C6シクロアルキル基、C1−C6ハロアルキル基、C2−C6アルケニル基、C1−C6アルコキシ基、C1−C6アルキルチオ基、C2−C6アルキニル基、ニトロ基、シアノ基、C1−C6アルキル基を有していてもよいアミノカルボニル基、C2−C6ハロアルケニル基、C2−C6ハロアルキニル基、C3−C6ハロシクロアルキル基、C1−C6ハロアルコキシ基、C1−C6ハロアルキルチオ基、C3−C6シクロアルキルオキシ基、C3−C6ハロシクロアルキルオキシ基、C3−C6シクロアルキルチオ基、C3−C6アルケニルオキシ基、C3−C6アルキニルオキシ基、C3−C6ハロアルケニルオキシ基、C3−C6ハロアルキニルオキシ基、C3−C6アルケニルチオ基、C3−C6アルキニルチオ基、C3−C6ハロアルケニルチオ基、C3−C6ハロアルキニルチオ基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C6アルキルカルボニルオキシ基、C2−C6アルキルカルボニルチオ基、C2−C6アルコキシカルボニル基、ヒドロキシ基、C1−C6アルキル基を有していてもよいアミノ基、ペンタフルオロスルファニル基、C3−C9トリアルキルシリル基、C5−C14トリアルキルシリルエチニル基、C1−C4アルキルスルホニル基、C1−C4ハロアルキルスルホニル基、C1−C4アルキルスルフィニル基、C1−C4ハロアルキルスルフィニル基、C2−C5アルコキシアルキル基またはC2−C5アルキルチオアルキル基を表す。〕[2] E is any one of groups selected from the group P 4, tetrazolinone compound according to [1].
Group P 4 : Group consisting of E1 to E7.
[In the formula, # represents a bonding position with a tetrazolinone ring, and $ represents a bonding position with Y. Z 1 represents a nitrogen atom or CR 1 ; Z 2 represents a nitrogen atom or CR 2 ; Z 3 represents a nitrogen atom or CR 3 ; Z 4 represents a nitrogen atom or CR 4 ;
Y 1 represents an oxygen atom, a sulfur atom or NR 8 ; Y 2 represents an oxygen atom, a sulfur atom or NR 6 ; Y 3 represents an oxygen atom, a sulfur atom or NR 7 ;
R 1 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, halogen atom, C1-C6 haloalkyl group, C2-C6 alkenyl group, C1-C6 alkoxy group, C1-C6 alkylthio group, C2-C6. An aminocarbonyl group optionally having an alkynyl group, a nitro group, a cyano group, a C1-C6 alkyl group,
C2-C6 haloalkenyl group, C2-C6 haloalkynyl group, C3-C6 halocycloalkyl group, C1-C6 haloalkoxy group, C1-C6 haloalkylthio group, C3-C6 cycloalkyloxy group, C3-C6 halocycloalkyl group Oxy group, C3-C6 cycloalkylthio group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C3-C6 haloalkenyloxy group, C3-C6 haloalkynyloxy group, C3-C6 alkenylthio group, C3-C6 Alkynylthio group, C3-C6 haloalkenylthio group, C3-C6 haloalkynylthio group, C2-C6 alkylcarbonyl group, C2-C6 haloalkylcarbonyl group, C2-C6 alkylcarbonyloxy group, C2-C6 alkylcarbonylthio group, C2-C6 alkoxycarbo Group, hydroxy group, thiol group, amino group optionally having C1-C6 alkyl group, pentafluorosulfanyl group, C3-C9 trialkylsilyl group, C5-C14 trialkylsilylethynyl group, C1-C4 alkyl group Represents a sulfonyl group, a C1-C4 haloalkylsulfonyl group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C2-C5 alkoxyalkyl group or a C2-C5 alkylthioalkyl group;
R 2 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C2-C3 haloalkenyl group or a C1-C3 alkoxy group. Represents;
R 6 and R 7 each independently represents a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C2-C3 haloalkenyl group or a C1-C3 alkoxy group;
R 8 is a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C2-C6 alkynyl group, Nitro group, cyano group, aminocarbonyl group optionally having C1-C6 alkyl group, C2-C6 haloalkenyl group, C2-C6 haloalkynyl group, C3-C6 halocycloalkyl group, C1-C6 haloalkoxy group , C1-C6 haloalkylthio group, C3-C6 cycloalkyloxy group, C3-C6 halocycloalkyloxy group, C3-C6 cycloalkylthio group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C3-C6 halo Alkenyloxy group, C3-C6 haloalkynyloxy group, C3-C6 alkeni Ruthio group, C3-C6 alkynylthio group, C3-C6 haloalkenylthio group, C3-C6 haloalkynylthio group, C2-C6 alkylcarbonyl group, C2-C6 haloalkylcarbonyl group, C2-C6 alkylcarbonyloxy group, C2- C6 alkylcarbonylthio group, C2-C6 alkoxycarbonyl group, hydroxy group, amino group optionally having C1-C6 alkyl group, pentafluorosulfanyl group, C3-C9 trialkylsilyl group, C5-C14 trialkylsilyl group An ethynyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C2-C5 alkoxyalkyl group or a C2-C5 alkylthioalkyl group is represented. ]
〔3〕 Yが−O−CH2−である〔1〕または〔2〕に記載のテトラゾリノン化合物。
〔4〕 〔1〕〜〔3〕いずれか一に記載のテトラゾリノン化合物を含有する有害生物防除剤。
〔5〕 〔1〕〜〔3〕いずれか一に記載のテトラゾリノン化合物の有効量を植物又は土壌に施用する有害生物の防除方法。
〔6〕 有害生物を防除するための〔1〕〜〔3〕いずれか一に記載のテトラゾリノン化合物の使用。
本発明により、有害生物を防除することができる。[3] The tetrazolinone compound according to [1] or [2], wherein Y is —O—CH 2 —.
[4] A pest control agent comprising the tetrazolinone compound according to any one of [1] to [3].
[5] A method for controlling pests, wherein an effective amount of the tetrazolinone compound according to any one of [1] to [3] is applied to a plant or soil.
[6] Use of the tetrazolinone compound according to any one of [1] to [3] for controlling pests.
According to the present invention, pests can be controlled.
本発明の化合物は、式(1)
〔R5、X、E、Y、Q及びAは前記と同じ意味を表す。〕
で示されるテトラゾリノン化合物(以下、本発明化合物と記載する。)である。The compounds of the present invention have the formula (1)
[R 5 , X, E, Y, Q, and A represent the same meaning as described above. ]
Is a tetrazolinone compound (hereinafter referred to as the present compound).
本明細書における置換基について、下記に記す。
本発明において、「員」とは、アリール、ヘテロ環、ヘテロアリール等の環を構成する原子の数を表す。例えば、ナフタレンであれば10員と表し、下記のベンゾフランであれば、9員と表す。
The substituents in this specification are described below.
In the present invention, the “member” represents the number of atoms constituting a ring such as aryl, heterocycle, heteroaryl and the like. For example, naphthalene is represented as 10 members, and the following benzofuran is represented as 9 members.
ハロゲン原子としては、フッ素原子、塩素原子、臭素原子およびヨウ素原子があげられる。
C1−C3アルキル基とは、メチル基、エチル基、プロピル基およびイソプロピル基があげられる。
1以上のハロゲン原子を有していてもよいC1−C3アルキル基とは、C1−C3アルキル基の1以上の水素原子がハロゲン原子で置換されていてもよいC1−C3アルキル基を表し、例えば、メチル基、エチル基、プロピル基、イソプロピル基、フルオロメチル基、クロロメチル基、ジフルオロメチル基、トリフルオロメチル基、2,2,2−トリフルオロエチル基、ペンタフルオロエチル基、2,2−ジフルオロエチル基、2−フルオロプロピル基、3−フルオロプロピル基、2,2−ジフルオロプロピル基、3,3,3−トリフルオロプロピル基および3−(フルオロメチル)−2−フルオロエチル基があげられる。Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
The C1-C3 alkyl group includes a methyl group, an ethyl group, a propyl group, and an isopropyl group.
The C1-C3 alkyl group optionally having one or more halogen atoms represents a C1-C3 alkyl group in which one or more hydrogen atoms of the C1-C3 alkyl group may be substituted with a halogen atom. , Methyl group, ethyl group, propyl group, isopropyl group, fluoromethyl group, chloromethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, 2,2- Examples include difluoroethyl group, 2-fluoropropyl group, 3-fluoropropyl group, 2,2-difluoropropyl group, 3,3,3-trifluoropropyl group, and 3- (fluoromethyl) -2-fluoroethyl group. .
5員ヘテロアリール基とは、窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を環構成原子として含有する基を表し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。
2価の5員ヘテロアリール基としては、例えば、チオフェン−ジ−イル基、フラン−ジ−イル基、ピロール−ジ−イル基、ピラゾール−ジ−イル基、イミダゾール−ジ−イル基、チアゾール−ジ−イル基、イソチアゾール−ジ−イル基、オキサゾール−ジ−イル基、イソキサゾール−ジ−イル基、トリアゾール−ジ−イル基、オキサジアゾール−ジ−イル基およびチアジアゾール−ジ−イル基があげられる。。
例えば、下記の基E11〜E46(式中、#はテトラゾリノン環との結合位置を表し、$はYとの結合位置を表す。)が挙げられる。
〔式中、R1、R2、R3、R4、R5、R6、R7及びR8は前記と同じ意味を表す。〕The 5-membered heteroaryl group represents a group containing one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a ring atom, and when containing two or more atoms, the atoms are the same Or they may be different.
Examples of the divalent 5-membered heteroaryl group include thiophene-di-yl group, furan-di-yl group, pyrrole-di-yl group, pyrazol-di-yl group, imidazole-di-yl group, and thiazole- Di-yl, isothiazol-di-yl, oxazol-di-yl, isoxazol-di-yl, triazol-di-yl, oxadiazole-di-yl and thiadiazol-di-yl can give. .
For example, the following groups E11 to E46 (in the formula, # represents a bonding position with a tetrazolinone ring, and $ represents a bonding position with Y).
[Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 represent the same meaning as described above. ]
6員ヘテロアリール基とは、窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を環構成原子として含有する基を表し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。
2価の6員ヘテロアリール基としては、例えば、ピリジン−ジ−イル基、ピリミジン−ジ−イル基、ピラジン−ジ−イル基、ピリダジン−ジ−イル基、トリアジン−ジ−イル基およびテトラジン−ジ−イル基があげられる。
例えば、下記の基E50〜E65(式中、#はテトラゾリノン環との結合位置を表し、$はYとの結合位置を表す。)が挙げられる。;
〔式中、R1、R2、R3、R4、R5、R6、R7及びR8は前記と同じ意味を表す。〕
2価のC6−C10アリール基としては、例えば、ベンゼン−1,2−ジ−イル基、ベンゼン−1,3−ジ−イル基、ベンゼン−1,4−ジ−イル基、ナフタレン−1,2−ジ−イル基、ナフチル−1,6−ジ−イル基およびナフチル−1,8−ジ−イル基が挙げられる。The 6-membered heteroaryl group represents a group containing one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a ring-constituting atom, and when containing two or more atoms, the atoms are the same Or they may be different.
Examples of the divalent 6-membered heteroaryl group include pyridine-di-yl group, pyrimidine-di-yl group, pyrazin-di-yl group, pyridazine-di-yl group, triazine-di-yl group and tetrazine- And di-yl group.
For example, the following groups E50 to E65 (in the formula, # represents a bonding position with a tetrazolinone ring and $ represents a bonding position with Y). ;
[Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 represent the same meaning as described above. ]
Examples of the divalent C6-C10 aryl group include benzene-1,2-di-yl group, benzene-1,3-di-yl group, benzene-1,4-di-yl group, naphthalene-1, Examples include 2-di-yl group, naphthyl-1,6-di-yl group, and naphthyl-1,8-di-yl group.
5−10員ヘテロ環基とは、窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を環構成原子として含有する基を表し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。
2価の5−10員ヘテロ環基としては、例えば、ピリジン−ジ−イル基、ピリミジン−ジ−イル基、ピラジン−ジ−イル基、ピリダジン−ジ−イル基、チオフェン−ジ−イル基、フラン−ジ−イル基、ピロール−ジ−イル基、ピラゾール−ジ−イル基、イミダゾール−ジ−イル基、チアゾール−ジ−イル基、イソチアゾール−ジ−イル基、オキサゾール−ジ−イル基、イソキサゾール−ジ−イル基、トリアゾール−ジ−イル基、テトラゾール−ジ−イル基、オキサジアゾール−ジ−イル基、チアジアゾール−ジ−イル基、ベンゾフラン−ジ−イル基、ベンゾチオフェン−ジ−イル基、インドール−ジ−イル基、ベンゾイミダゾール−ジ−イル基、インダゾール−ジ−イル基、ベンゾチアゾール−ジ−イル基、ベンゾオキサゾール−ジ−イル基、ベンゾイソチアゾール−ジ−イル基、ベンゾイソキサゾール−ジ−イル基、ピラゾロピロール−ジ−イル基、ピラゾロピラゾール−ジ−イル基、ピラゾロイミダゾール−ジ−イル基、イミダゾピリミジン−ジ−イル基、イミダゾピラジン−ジ−イル基、トリアゾピリジン−ジ−イル基、トリアゾピリミジン−ジ−イル基、トリアゾキノリン−ジ−イル基、2,3−ジヒドロベンゾフラン−ジ−イル基、2,3−ジヒドロベンゾチオフェン−ジ−イル基、1,3−ベンゾジオキソール−ジ−イル基、キノリン−ジ−イル基、イソキノリン−ジ−イル基、シンノリン−ジ−イル基、フタラジン−ジ−イル基、キナゾリン−ジ−イル基、キノキサリン−ジ−イル基、ナフチリジン−ジ−イル基、クロマン−ジ−イル基、イソクロマン−ジ−イル基、チエノピリジン−ジ−イル基、チエノピラゾール−ジ−イル基およびチエノキノリン−ジ−イル基があげられ、好ましくはピラゾール−ジ−イル基およびチアゾール−ジ−イル基があげられる。
例えば、下記の基Q1〜Q366(式中、#はYとの結合位置を表し、$はAとの結合位置を表す。)が挙げられる。The 5- to 10-membered heterocyclic group represents a group containing one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as a ring constituent atom, and when containing two or more atoms, May be the same or different.
Examples of the divalent 5-10 membered heterocyclic group include a pyridine-di-yl group, a pyrimidine-di-yl group, a pyrazine-di-yl group, a pyridazine-di-yl group, a thiophene-di-yl group, Furan-di-yl group, pyrrole-di-yl group, pyrazole-di-yl group, imidazole-di-yl group, thiazol-di-yl group, isothiazol-di-yl group, oxazol-di-yl group, Isoxazol-di-yl group, triazol-di-yl group, tetrazole-di-yl group, oxadiazole-di-yl group, thiadiazol-di-yl group, benzofuran-di-yl group, benzothiophene-di-yl Group, indole-di-yl group, benzimidazol-di-yl group, indazole-di-yl group, benzothiazol-di-yl group, benzoxazol-di-yl group Benzoisothiazol-di-yl group, benzoisoxazol-di-yl group, pyrazolopyrrole-di-yl group, pyrazolopyrazol-di-yl group, pyrazoloimidazole-di-yl group, imidazopyrimidine-di -Yl group, imidazopyrazin-di-yl group, triazopyridin-di-yl group, triazopyrimidin-di-yl group, triazoquinolin-di-yl group, 2,3-dihydrobenzofuran-di-yl group 2,3-dihydrobenzothiophene-di-yl group, 1,3-benzodioxol-di-yl group, quinolin-di-yl group, isoquinolin-di-yl group, cinnoline-di-yl group, phthalazine -Di-yl group, quinazoline-di-yl group, quinoxaline-di-yl group, naphthyridin-di-yl group, chroman-di-yl group, isochroman-di-yl group Thienopyridine - di - yl group, Chienopirazoru - di - yl group and Chienokinorin - di - yl group, and preferably a pyrazole - di - yl group, and a thiazole - di - yl group.
For example, the following groups Q1 to Q366 (in the formula, # represents a bonding position with Y and $ represents a bonding position with A).
〔式中、R30、R31、R32、R33、R34、R35、R36、R37、R38、R40、R41、R42およびR43はそれぞれ独立して、水素原子、ハロゲン原子、シアノ基、C3−C6シクロアルキル基、C3−C6ハロシクロアルキル基、C1−C4アルコキシ基、C1−C4ハロアルコキシ基、C1−C4アルキルチオ基またはC1−C4ハロアルキルチオ基を表し;
R39は、水素原子、シアノ基、C3−C6シクロアルキル基、C3−C6ハロシクロアルキル基、C1−C4アルコキシ基、C1−C4ハロアルコキシ基、C1−C4アルキルチオ基またはC1−C4ハロアルキルチオ基を表す。〕 [Wherein R 30 , R 31 , R 32 , R 33 , R 34 , R 35 , R 36 , R 37 , R 38 , R 40 , R 41 , R 42 and R 43 are each independently a hydrogen atom Represents a halogen atom, a cyano group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group or a C1-C4 haloalkylthio group;
R 39 is a hydrogen atom, a cyano group, a C3-C6 cycloalkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group or a C1-C4 haloalkylthio group. Represents. ]
C6−C10アリール基とは、具体的には、フェニル基、1−ナフチル基および2−ナフチル基を表す。
C6−C10アリールオキシ基とは、具体的には、フェノキシ基、1−ナフチルオキシ基および2−ナフチルオキシ基を表す。
C6−C10アリールチオ基とは、具体的には、フェニルチオ基、1−ナフチルチオ基および2−ナフチルチオ基を表す。
C6−C10アリールアミノ基とは、具体的には、フェニルアミノ基、(1−ナフチル)アミノ基および(2−ナフチル)アミノ基を表す。
C3−C10シクロアルキル基とは、具体的には、シクロプロピル基、シクロブチル基、シクロペンチル基、シクロヘキシル基、シクロヘプチル基、シクロオクチル基、シクロノニル基およびシクロデシル基を表す。
C6−C10アリールスルホニル基とは、具体的には、フェニルスルホニル基、1−ナフチルスルホニル基および2−ナフチルスルホニル基を表す。
C6−C10アリールスルフィニル基とは、具体的には、フェニルスルフィニル基、1−ナフチルフィニル基および2−ナフチルスルフィニル基を表す。The C6-C10 aryl group specifically represents a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
Specifically, the C6-C10 aryloxy group represents a phenoxy group, a 1-naphthyloxy group, and a 2-naphthyloxy group.
A C6-C10 arylthio group specifically represents a phenylthio group, a 1-naphthylthio group, and a 2-naphthylthio group.
The C6-C10 arylamino group specifically represents a phenylamino group, a (1-naphthyl) amino group, and a (2-naphthyl) amino group.
The C3-C10 cycloalkyl group specifically represents a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, and a cyclodecyl group.
The C6-C10 arylsulfonyl group specifically represents a phenylsulfonyl group, a 1-naphthylsulfonyl group, and a 2-naphthylsulfonyl group.
The C6-C10 arylsulfinyl group specifically represents a phenylsulfinyl group, a 1-naphthylfinyl group, and a 2-naphthylsulfinyl group.
5−10員ヘテロ環基としては、例えば、ピリジル基、ピリミジニル基、ピラジニル基、ピリダジニル基、チエニル基、フリル基、ピロリル基、ピラゾリル基、イミダゾリル基、チアゾリル基、イソチアゾリル基、オキサゾリル基、イソキサゾリル基、トリアゾリル基、テトラゾリル基、オキサゾアゾリル基、チアジアゾリル基、ベンゾフリル基、ベンゾチエニル基、インドリル基、ベンゾイミダゾリル基、インダゾリル基、ベンゾチアゾリル基、ベンゾオキサゾリル基、ベンゾイソチアゾリル基、ベンゾイソキサゾリル基、ピラゾロピロリル基、ピラゾロピラゾリル基、ピラゾロイミダゾリル基、イミダゾピリミジニル基、イミダゾピラジニル基、トリアゾロピリジル基、トリアゾロピリミジニル基、トリアゾロキノリル基、2,3−ジヒドロベンゾフリル基、2,3−ジヒドロベンゾチエニル基、1,3−ベンゾジオキソリル基、キノリル基、イソキノリル基、シンノリニル基、フタラジニル基、キナゾリニル基、キノキサリニル基、ナフチリジニル基、クロマニル基、イソクロマニル基、チエノピリジル基、チエノピラゾリル基およびチエノキノリル基があげられ、好ましくはピリジル基があげられる。
例えば、下記の基A1〜A133(式中、#はQとの結合部位を表す。)が挙げられる。
Examples of the 5- to 10-membered heterocyclic group include pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, thienyl group, furyl group, pyrrolyl group, pyrazolyl group, imidazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group , Triazolyl group, tetrazolyl group, oxazoazolyl group, thiadiazolyl group, benzofuryl group, benzothienyl group, indolyl group, benzoimidazolyl group, indazolyl group, benzothiazolyl group, benzoxazolyl group, benzoisothiazolyl group, benzoisoxazolyl group , Pyrazolopyrrolyl group, pyrazolopyrazolyl group, pyrazoloimidazolyl group, imidazopyrimidinyl group, imidazopyrazinyl group, triazolopyridyl group, triazolopyrimidinyl group, triazoloquinolyl group, 2,3-dihi Lobenzofuryl group, 2,3-dihydrobenzothienyl group, 1,3-benzodioxolyl group, quinolyl group, isoquinolyl group, cinnolinyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, naphthyridinyl group, chromanyl group, isochromanyl group, thienopyridyl group Group, thienopyrazolyl group and thienoquinolyl group, preferably pyridyl group.
For example, the following groups A1 to A133 (wherein # represents a binding site with Q) can be mentioned.
[式中、R50、R51、R52、R53、R54、R55、R56、R57、R58、R60、R61、R62およびR63はそれぞれ独立して、水素原子、ハロゲン原子、C1−C6アルキル基、C1−C6ハロアルキル基、C2−C6アルケニル基、C2−C6ハロアルケニル基、C2−C6アルキニル基、C2−C6ハロアルキニル基、C3−C6シクロアルキル基、C3−C6ハロシクロアルキル基、C1−C6アルコキシ基、C1−C6ハロアルコキシ基、C1−C6アルキルチオ基、C1−C6ハロアルキルチオ基、C3−C6シクロアルキルオキシ基、C3−C6ハロシクロアルキルオキシ基、C3−C6シクロアルキルチオ基、C3−C6アルケニルオキシ基、C3−C6アルキニルオキシ基、C3−C6ハロアルケニルオキシ基、C3−C6ハロアルキニルオキシ基、C3−C6アルケニルチオ基、C3−C6アルキニルチオ基、C3−C6ハロアルケニルチオ基、C3−C6ハロアルキニルチオ基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C6アルキルカルボニルオキシ基、C2−C6アルキルカルボニルチオ基、カルボキシ基、ホルミル基、C2−C6アルコキシカルボニル基、ニトロ基、シアノ基、ヒドロキシ基、C1−C6アルキルスルホニル基、C1−C6ハロアルキルスルホニル基、C1−C6アルキルスルフィニル基、C1−C6ハロアルキルスルフィニル基、C1−C6アルキル基を有していてもよいアミノ基、C1−C6アルキル基を有していてもよいアミノスルホニル基またはC1−C6アルキル基を有していてもよいアミノカルボニル基を表し;
R59は、水素原子、C1−C6アルキル基、C1−C6ハロアルキル基、C2−C6アルケニル基、C2−C6ハロアルケニル基、C2−C6アルキニル基、C2−C6ハロアルキニル基、C3−C6シクロアルキル基、C3−C6ハロシクロアルキル基、C1−C6アルコキシ基、C1−C6ハロアルコキシ基、C1−C6アルキルチオ基、C1−C6ハロアルキルチオ基、C3−C6シクロアルキルオキシ基、C3−C6ハロシクロアルキルオキシ基、C3−C6シクロアルキルチオ基、C3−C6アルケニルオキシ基、C3−C6アルキニルオキシ基、C3−C6ハロアルケニルオキシ基、C3−C6ハロアルキニルオキシ基、C3−C6アルケニルチオ基、C3−C6アルキニルチオ基、C3−C6ハロアルケニルチオ基、C3−C6ハロアルキニルチオ基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C6アルキルカルボニルオキシ基、C2−C6アルキルカルボニルチオ基、ホルミル基、C2−C6アルコキシカルボニル基、ニトロ基、シアノ基、ヒドロキシ基、C1−C6アルキルスルホニル基、C1−C6ハロアルキルスルホニル基、C1−C6アルキルスルフィニル基、C1−C6ハロアルキルスルフィニル基、C1−C6アルキル基を有していてもよいアミノ基、C1−C6アルキル基を有していてもよいアミノスルホニル基またはC1−C6アルキル基を有していてもよいアミノカルボニル基を表す。] [Wherein R 50 , R 51 , R 52 , R 53 , R 54 , R 55 , R 56 , R 57 , R 58 , R 60 , R 61 , R 62 and R 63 are each independently a hydrogen atom , Halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 haloalkynyl group, C3-C6 cycloalkyl group, C3 -C6 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C3-C6 cycloalkyloxy group, C3-C6 halocycloalkyloxy group, C3-C6 cycloalkylthio group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C3-C Haloalkenyloxy group, C3-C6 haloalkynyloxy group, C3-C6 alkenylthio group, C3-C6 alkynylthio group, C3-C6 haloalkenylthio group, C3-C6 haloalkynylthio group, C2-C6 alkylcarbonyl group, C2-C6 haloalkylcarbonyl group, C2-C6 alkylcarbonyloxy group, C2-C6 alkylcarbonylthio group, carboxy group, formyl group, C2-C6 alkoxycarbonyl group, nitro group, cyano group, hydroxy group, C1-C6 alkylsulfonyl Group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, amino group optionally having C1-C6 alkyl group, optionally having C1-C6 alkyl group An aminosulfonyl group or Optionally having 1-C6 alkyl group represents an amino group;
R 59 is a hydrogen atom, a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C6 cycloalkyl group. Group, C3-C6 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C3-C6 cycloalkyloxy group, C3-C6 halocycloalkyl group Oxy group, C3-C6 cycloalkylthio group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C3-C6 haloalkenyloxy group, C3-C6 haloalkynyloxy group, C3-C6 alkenylthio group, C3-C6 Alkynylthio group, C3-C6 haloalkenylthio group, C3- C6 haloalkynylthio group, C2-C6 alkylcarbonyl group, C2-C6 haloalkylcarbonyl group, C2-C6 alkylcarbonyloxy group, C2-C6 alkylcarbonylthio group, formyl group, C2-C6 alkoxycarbonyl group, nitro group, cyano Group, hydroxy group, C1-C6 alkylsulfonyl group, C1-C6 haloalkylsulfonyl group, C1-C6 alkylsulfinyl group, C1-C6 haloalkylsulfinyl group, amino group optionally having C1-C6 alkyl group, C1- The aminosulfonyl group which may have a C6 alkyl group, or the aminocarbonyl group which may have a C1-C6 alkyl group is represented. ]
5−10員ヘテロアリールとは、窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を環構成原子として含有し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい5−10員のヘテロアリールを表し、例えば、ピリジン、ピリミジン、ピラジン、ピリダジン、チオフェン、フラン、ピロール、およびオキサゾールが挙げられる。
5−10員ヘテロアリールオキシ基としては、例えば、ピリジルオキシ基、ピリミジニルオキシ基、ピラジニルオキシ基、ピリダジニルオキシ基、チエニルオキシ基、フリルオキシ基、ピロリルオキシ基、ピラゾリルオキシ基、イミダゾリルオキシ基、チアゾリルオキシ基、イソチアゾリルオキシ基、オキサゾリルオキシ基、イソキサゾリルオキシ基、トリアゾリルオキシ基、テトラゾリルオキシ基、オキサゾアゾリルオキシ基、チアジアゾリルオキシ基、ベンゾフリルオキシ基、ベンゾチエニルオキシ基、インドリルオキシ基、ベンゾイミダゾリルオキシ基、インダゾリルオキシ基、ベンゾチアゾリルオキシ基、ベンゾオキサゾリルオキシ基、ベンゾイソチアゾリルオキシ基、ベンゾイソキサゾリルオキシ基、ピラゾロピロリルオキシ基、ピラゾロピラゾリルオキシ基、ピラゾロイミダゾリルオキシ基、イミダゾピリミジニルオキシ基、イミダゾピラジニルオキシ基、トリアゾロピリジルオキシ基、トリアゾロピリミジニルオキシ基、トリアゾロキノリルオキシ基、2,3−ジヒドロベンゾフリルオキシ基、2,3−ジヒドロベンゾチエニルオキシ基、1,3−ベンゾジオキソリルオキシ基、キノリルオキシ基、イソキノリルオキシ基、シンノリニルオキシ基、フタラジニルオキシ基、キナゾリニルオキシ基、キノキサリニルオキシ基、ナフチリジニルオキシ基、クロマニルオキシ基、イソクロマニルオキシ基、チエノピリジルオキシ基、チエノピラゾリルオキシ基およびチエノキノリルオキシ基があげられる。The 5- to 10-membered heteroaryl includes one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring constituent atoms, and when two or more atoms are contained, the atoms are the same or phase Represents 5-10 membered heteroaryl, which may be different, including, for example, pyridine, pyrimidine, pyrazine, pyridazine, thiophene, furan, pyrrole, and oxazole.
Examples of 5-10 membered heteroaryloxy groups include pyridyloxy, pyrimidinyloxy, pyrazinyloxy, pyridazinyloxy, thienyloxy, furyloxy, pyrrolyloxy, pyrazolyloxy, imidazolyloxy, thiazolyloxy Group, isothiazolyloxy group, oxazolyloxy group, isoxazolyloxy group, triazolyloxy group, tetrazolyloxy group, oxazoazolyloxy group, thiadiazolyloxy group, benzofuryloxy group , Benzothienyloxy group, indolyloxy group, benzimidazolyloxy group, indazolyloxy group, benzothiazolyloxy group, benzoxazolyloxy group, benzoisothiazolyloxy group, benzoisoxazolyloxy group, Pyrazolopyrrolyloxy group, Lazolopyrazolyloxy group, pyrazoloimidazolyloxy group, imidazopyrimidinyloxy group, imidazopyrazinyloxy group, triazolopyridyloxy group, triazolopyrimidinyloxy group, triazoloquinolyloxy group, 2,3-dihydrobenzofuryloxy Group, 2,3-dihydrobenzothienyloxy group, 1,3-benzodioxolyloxy group, quinolyloxy group, isoquinolyloxy group, cinnolinyloxy group, phthalazinyloxy group, quinazolinyloxy group, Examples thereof include quinoxalinyloxy group, naphthyridinyloxy group, chromanyloxy group, isochromanyloxy group, thienopyridyloxy group, thienopyrazolyloxy group, and thienoquinolyloxy group.
5−10員ヘテロアリールチオ基としては、例えば、ピリジルチオ基、ピリミジニルチオ基、ピラジニルチオ基、ピリダジニルチオ基、チエニルチオ基、フリルチオ基、ピロリルチオ基、ピラゾリルチオ基、イミダゾリルチオ基、チアゾリルチオ基、イソチアゾリルチオ基、オキサゾリルチオ基、イソキサゾリルチオ基、トリアゾリルチオ基、テトラゾリルチオ基、オキサゾアゾリルチオ基、チアジアゾリルチオ基、ベンゾフリルチオ基、ベンゾチエニルチオ基、インドリルチオ基、ベンゾイミダゾリルチオ基、インダゾリルチオ基、ベンゾチアゾリルチオ基、ベンゾオキサゾリルチオ基、ベンゾイソチアゾリルチオ基、ベンゾイソキサゾリルチオ基、ピラゾロピロリルチオ基、ピラゾロピラゾリルチオ基、ピラゾロイミダゾリルチオ基、イミダゾピリミジニルチオ基、イミダゾピラジニルチオ基、トリアゾロピリジルチオ基、トリアゾロピリミジニルチオ基、トリアゾロキノリルチオ基、2,3−ジヒドロベンゾフリルチオ基、2,3−ジヒドロベンゾチエニルチオ基、1,3−ベンゾジオキソリルチオ基、キノリルチオ基、イソキノリルチオ基、シンノリニルチオ基、フタラジニルチオ基、キナゾリニルチオ基、キノキサリニルチオ基、ナフチリジニルチオ基、クロマニルチオ基、イソクロマニルチオ基、チエノピリジルチオ基、チエノピラゾリルチオ基およびチエノキノリルチオ基があげられる。 Examples of 5-10 membered heteroarylthio groups include pyridylthio, pyrimidinylthio, pyrazinylthio, pyridazinylthio, thienylthio, furylthio, pyrrolylthio, pyrazolylthio, imidazolylthio, thiazolylthio, isothiazolylthio Group, oxazolylthio group, isoxazolylthio group, triazolylthio group, tetrazolylthio group, oxazoazolylthio group, thiadiazolylthio group, benzofurylthio group, benzothienylthio group, indolylthio group, benzoimidazolylthio group, indazolylthio group, Benzothiazolylthio group, benzoxazolylthio group, benzoisothiazolylthio group, benzoisoxazolylthio group, pyrazolopyrrolylthio group, pyrazolopyrazolylthio group, pyrazoloimidazolylthio group, i Dazopyrimidinylthio group, imidazopyrazinylthio group, triazolopyridylthio group, triazolopyrimidinylthio group, triazoloquinolylthio group, 2,3-dihydrobenzofurylthio group, 2,3-dihydrobenzothienylthio group, 1,3-benzodioxolylthio group, quinolylthio group, isoquinolylthio group, cinnolinylthio group, phthalazinylthio group, quinazolinylthio group, quinoxalinylthio group, naphthyridinylthio group, chromanylthio group, isochromylthio group, thienopyridylthio Group, thienopyrazolylthio group and thienoquinolylthio group.
5−10員ヘテロアリールアミノ基とは、アミノ基の窒素上の1の水素原子が5−10員ヘテロアリール基で置換されている基を表し、例えば、ピリジルアミノ基、ピリミジルアミノ基、ピラジルアミノ基、ピリダジルアミノ基、チエニルアミノ基、フリルアミノ基、ピロリルアミノ基、ピラゾリルアミノ基、イミダゾリルアミノ基、チアゾリルアミノ基、イソチアゾリルアミノ基、オキサゾリルアミノ基、イソキサゾリルアミノ基、トリアゾリルアミノ基、テトラゾリルアミノ基、オキサゾアゾリルアミノ基、チアジアゾリルアミノ基、ベンゾフリルアミノ基、ベンゾチエニルアミノ基、インドリルアミノ基、ベンゾイミダゾリルアミノ基、インダゾリルアミノ基、ベンゾチアゾリルアミノ基、ベンゾオキサゾリルアミノ基、ベンゾイソチアゾリルアミノ基、ベンゾイソキサゾリルアミノ基、ピラゾロピロリルアミノ基、ピラゾロピラゾリルアミノ基、ピラゾロイミダゾリルアミノ基、イミダゾピリミジルアミノ基、イミダゾピラジルアミノ基、トリアゾピリジルアミノ基、トリアゾピリミジルアミノ基、トリアゾキノリルアミノ基、2,3−ジヒドロベンゾフリルアミノ基、2,3−ジヒドロベンゾチエニルアミノ基、1,3−ベンゾジオキソールイルアミノ基、キノリルアミノ基、イソキノリルアミノ基、シンノリニルアミノ基、フタラジニルアミノ基、キナゾリニルアミノ基、キノキサリルアミノ基、ナフチリジニルアミノ基、クロマニルアミノ基、イソクロマニルアミノ基、チエノピリジルアミノ基、チエノピラゾリルアミノ基およびチエノキノリルアミノ基があげられる。 The 5-10 membered heteroarylamino group represents a group in which one hydrogen atom on the nitrogen of the amino group is substituted with a 5-10 membered heteroaryl group. For example, a pyridylamino group, a pyrimidylamino group, a pyrazylamino group, a pyridazylamino group Group, thienylamino group, furylamino group, pyrrolylamino group, pyrazolylamino group, imidazolylamino group, thiazolylamino group, isothiazolylamino group, oxazolylamino group, isoxazolylamino group, triazolylamino group, tetra Zolylamino group, oxazoazolylamino group, thiadiazolylamino group, benzofurylamino group, benzothienylamino group, indolylamino group, benzoimidazolylamino group, indazolylamino group, benzothiazolylamino group, Benzoxazolylamino group, benzoisothi Zolylamino group, benzisoxazolylamino group, pyrazolopyrrolylamino group, pyrazolopyrazolylamino group, pyrazoloimidazolylamino group, imidazopyrimidylamino group, imidazopyrazylamino group, triazopyridylamino group, triazo Pyrimidylamino group, triazoquinolylamino group, 2,3-dihydrobenzofurylamino group, 2,3-dihydrobenzothienylamino group, 1,3-benzodioxolylamino group, quinolylamino group, isoquino Rylamino group, cinnolinylamino group, phthalazinylamino group, quinazolinylamino group, quinoxalylamino group, naphthyridinylamino group, chromanylamino group, isochromanylamino group, thienopyridylamino group, thieno And pyrazolylamino group and thienoquinolylamino group. .
C1−C6アルキル基としては、例えば、メチル基、エチル基、プロピル基、イソプロピル基、ブチル基、イソブチル基、sec−ブチル基、tert−ブチル基、ペンチル基および、およびヘキシル基が挙げられる。
C1−C6ハロアルキル基とは、C1−C6アルキル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、フルオロメチル基、クロロメチル基、ジクロロメチル基、ジフルオロメチル基、トリフルオロメチル基、トリクロロメチル基、トリブロモメチル基、クロロフルオロメチル基、ジクロロフルオロメチル基、2,2,2−トリフルオロエチル基、2,2,2−トリクロロエチル基、ペンタフルオロエチル基、クロロジフルオロメチル基、2,2−ジフルオロエチル基、2−クロロ−2−フルオロエチル基、2−クロロ−2,2−ジフルオロエチル基、2,2−ジクロロ−2−フルオロエチル基、2−フルオロプロピル基、3−フルオロプロピル基、2,2−ジフルオロプロピル基、3,3,3−トリフルオロプロピル基、3,4−ジフルオロブチル基、4−フルオロブチル基、5−フルオロペンチル基および2,2−ジフルオロヘキシル基が挙げられる。
C2−C6アルケニル基としては、例えば、ビニル基、1−プロペニル基、イソプロペニル基、2−プロペニル基、1−ブテニル基、1−メチル−1−プロペニル基、2−ブテニル基、1−メチル−2−プロペニル基、3−ブテニル基、2−メチル−1−プロペニル基、2−メチル−2−プロペニル基、1,3−ブタジエニル基、1−ペンテニル基、1−エチル−2−プロペニル基、2−ペンテニル基、1−メチル−1−ブテニル基、3−ペンテニル基、1−メチル−2−ブテニル基、4−ペンテニル基、1−メチル−3−ブテニル基、3−メチル−1−ブテニル基、1,2−ジメチル−2−プロペニル基、1,1−ジメチル−2−プロペニル基、2−メチル−2−ブテニル基、3−メチル−2−ブテニル基、1,2−ジメチル−1−プロペニル基、2−メチル−3−ブテニル基、3−メチル−3−ブテニル基、1,3−ペンタジエニル基、1−ビニル−2−プロペニル基、1−ヘキセニル基および5−ヘキセニル基が挙げられる。
C2−C6ハロアルケニル基とは、C2−C6アルケニル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、2−クロロビニル基、2−ブロモビニル基、2−ヨ−ドビニル基、1−トリフルオロメチルビニル基、1−トリフルオロメチル−2,2−ジフルオロビニル基、3,3−ジフルオロ−2−プロペニル基、ペルフルオロ−1−ブテニル基、ペルフルオロ−3−ブテニル基、ペルフルオロ−1−ペンテニル基、ペルフルオロ−4−ペンテニル基、ペルフルオロ−1−ヘキセニル基およびペルフルオロ−5−ヘキセニル基が挙げられる。
C2−C6アルキニル基としては、例えば、エチニル基、プロパルギル基、3−ブチン−2−イル基、2−ブチニル基、3−ブチニル基、2−メチル−3−ブチン−2−イル基、2−ペンチニル基、3−ペンチニル基、4−ペンチニル基、1−ヘキシニル基および5−ヘキシニル基が挙げられる。
C2−C6ハロアルキニル基とは、C2−C6アルキニル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、フルオロエチニル基、3‐クロロ‐2‐プロピニル基、3‐ブロモ‐2‐プロピニル基、3‐ヨード‐2‐プロピニル基、3‐クロロ‐1‐プロピニル基、5‐クロロ‐4‐ペンチニル基、3,3,3−トリフルオロ−1−プロピニル基、3,3,3−トリフルオロ−1−プロピニル基、ペルフルオロ−2−ブチニル基、ペルフルオロ−3−ブチニル基、ペルフルオロ−2−ペンチニル基、ペルフルオロ−3−ペンチニル基、ペルフルオロ−4−ペンチニル基、ペルフルオロ−1‐ヘキシニル基およびペルフルオロ−5‐ヘキシニル基が挙げられる。Examples of the C1-C6 alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, and a hexyl group.
The C1-C6 haloalkyl group represents a group in which at least one hydrogen atom of the C1-C6 alkyl group is substituted with a halogen atom. Fluoromethyl group, trichloromethyl group, tribromomethyl group, chlorofluoromethyl group, dichlorofluoromethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, chloro Difluoromethyl group, 2,2-difluoroethyl group, 2-chloro-2-fluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2-dichloro-2-fluoroethyl group, 2-fluoropropyl Group, 3-fluoropropyl group, 2,2-difluoropropyl group, 3,3,3-trifluoro Propyl group, 3,4-difluoro butyl group, 4-fluoro butyl group, and a 5-fluoropentyl group and 2,2-difluoro-hexyl group.
Examples of the C2-C6 alkenyl group include a vinyl group, 1-propenyl group, isopropenyl group, 2-propenyl group, 1-butenyl group, 1-methyl-1-propenyl group, 2-butenyl group, 1-methyl- 2-propenyl group, 3-butenyl group, 2-methyl-1-propenyl group, 2-methyl-2-propenyl group, 1,3-butadienyl group, 1-pentenyl group, 1-ethyl-2-propenyl group, 2 -Pentenyl group, 1-methyl-1-butenyl group, 3-pentenyl group, 1-methyl-2-butenyl group, 4-pentenyl group, 1-methyl-3-butenyl group, 3-methyl-1-butenyl group, 1,2-dimethyl-2-propenyl group, 1,1-dimethyl-2-propenyl group, 2-methyl-2-butenyl group, 3-methyl-2-butenyl group, 1,2-dimethyl-1-propene Group, 2-methyl-3-butenyl group, 3-methyl-3-butenyl group, 1,3-pentadienyl, 1-vinyl-2-propenyl group, and a 1-hexenyl group and 5-hexenyl.
The C2-C6 haloalkenyl group represents a group in which at least one hydrogen atom of the C2-C6 alkenyl group is substituted with a halogen atom, and examples thereof include a 2-chlorovinyl group, a 2-bromovinyl group, and 2-iodovinyl. Group, 1-trifluoromethylvinyl group, 1-trifluoromethyl-2,2-difluorovinyl group, 3,3-difluoro-2-propenyl group, perfluoro-1-butenyl group, perfluoro-3-butenyl group, perfluoro Examples include a -1-pentenyl group, a perfluoro-4-pentenyl group, a perfluoro-1-hexenyl group, and a perfluoro-5-hexenyl group.
Examples of the C2-C6 alkynyl group include ethynyl group, propargyl group, 3-butyn-2-yl group, 2-butynyl group, 3-butynyl group, 2-methyl-3-butyn-2-yl group, 2- Examples include a pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-hexynyl group, and a 5-hexynyl group.
The C2-C6 haloalkynyl group represents a group in which at least one hydrogen atom of the C2-C6 alkynyl group is substituted with a halogen atom, such as a fluoroethynyl group, 3-chloro-2-propynyl group, 3-bromo -2-propynyl group, 3-iodo-2-propynyl group, 3-chloro-1-propynyl group, 5-chloro-4-pentynyl group, 3,3,3-trifluoro-1-propynyl group, 3,3 , 3-trifluoro-1-propynyl group, perfluoro-2-butynyl group, perfluoro-3-butynyl group, perfluoro-2-pentynyl group, perfluoro-3-pentynyl group, perfluoro-4-pentynyl group, perfluoro-1- Examples include a hexynyl group and a perfluoro-5-hexynyl group.
C3−C6シクロアルキル基としては、例えば、シクロプロピル基、シクロブチル基、シクロペンチル基およびシクロヘキシル基が挙げられる。
C3−C6ハロシクロアルキル基とは、C3−C6シクロアルキル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、2−フルオロシクロプロピル基、2,2−ジフルオロシクロプロピル基、2−クロロ−2−フルオロシクロプロピル基、2,2−ジクロロシクロプロピル基、2,2−ジブロモシクロプロピル基、2,2,3,3−テトラフルオロシクロブチル基、2−クロロシクロペンチル基、2−クロロシクロヘキシル基、4,4−ジフルオロシクロヘキシル基および4−クロロシクロヘキシル基が挙げられる。
C1−C6アルコキシ基とは、アルコキシ基を表し、例えば、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、イソブトキシ基、sec−ブトキシ基、tert−ブトキシ基、ペンチルオキシ基、イソアミルオキシ基、ネオペンチルオキシ基、2−ペンチルオキシ基、3−ペンチルオキシ基、2−メチルブチルオキシ基、ヘキシルオキシ基、イソヘキシルオキシ基、3−メチルペンチルオキシ基および4−メチルペンチルオキシ基が挙げられる。
C1−C6ハロアルコキシ基とは、C1−C6アルコキシ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、トリフルオロメトキシ基、トリクロロメトキシ基、クロロメトキシ基、ジクロロメトキシ基、フルオロメトキシ基、ジフルオロメトキシ基、ペンタフルオロエトキシ基、2,2,2−トリフルオロエトキシ基、2−フルオロエトキシ基、2,2−ジフルオロエトキシ基、ヘプタフルオロプロポキシ基、3,3,3−トリフルオロプロポキン基、2−フルオロプロポキシ基、3−フルオロプロポキシ基、2,2−ジフルオロプロポキシ基、2,3−ジフルオロプロポキシ基、3,3,3−トリフルオロプロポキシ基、ノナフルオロブトキシ基、ペルフルオロペンチルオキシ基およびペルフルオロヘキシルオキシ基が挙げられる。Examples of the C3-C6 cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.
The C3-C6 halocycloalkyl group represents a group in which at least one hydrogen atom of the C3-C6 cycloalkyl group is substituted with a halogen atom, for example, a 2-fluorocyclopropyl group, 2,2-difluorocyclopropyl Group, 2-chloro-2-fluorocyclopropyl group, 2,2-dichlorocyclopropyl group, 2,2-dibromocyclopropyl group, 2,2,3,3-tetrafluorocyclobutyl group, 2-chlorocyclopentyl group 2-chlorocyclohexyl group, 4,4-difluorocyclohexyl group and 4-chlorocyclohexyl group.
C1-C6 alkoxy group represents an alkoxy group, for example, methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, isoamyloxy Group, neopentyloxy group, 2-pentyloxy group, 3-pentyloxy group, 2-methylbutyloxy group, hexyloxy group, isohexyloxy group, 3-methylpentyloxy group and 4-methylpentyloxy group It is done.
The C1-C6 haloalkoxy group represents a group in which at least one hydrogen atom of the C1-C6 alkoxy group is substituted with a halogen atom, such as a trifluoromethoxy group, a trichloromethoxy group, a chloromethoxy group, a dichloromethoxy group. , Fluoromethoxy group, difluoromethoxy group, pentafluoroethoxy group, 2,2,2-trifluoroethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, heptafluoropropoxy group, 3,3,3- Trifluoropropoxy group, 2-fluoropropoxy group, 3-fluoropropoxy group, 2,2-difluoropropoxy group, 2,3-difluoropropoxy group, 3,3,3-trifluoropropoxy group, nonafluorobutoxy group, Perfluoropentyloxy group and perfluorohexyl Include oxy group.
C1−C6アルキルチオ基としては、例えば、メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、ブチルチオ基、イソブチルチオ基、sec−ブチルチオ基、tert−ブチルチオ基、ペンチルチオ基、イソペンチルチオ基、ネオペンチルチオ基、イソアミルチオ基、2−ペンチルチオ基、3−ペンチルチオ基、2−メチルブチルチオ基、ヘキシルチオ基、イソヘキシルチオ基、sec−ヘキシルチオ基、3−メチルペンチルチオ基および4−メチルペンチルチオ基が挙げられる。
C1−C6ハロアルキルチオ基とは、直鎖状もしくは分枝状のC1−C6アルキルチオ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、フルオロメチルチオ基、ジフルオロメチルチオ基、トリフルオロメチルチオ基、ペンタフルオロエチルチオ基、2,2,2−トリフルオロエチルチオ基、2,2−ジフルオロエチルチオ基、ヘプタフルオロプロピルチオ基、3,3,3−トリフルオロプロピルチオ基、2,2−ジフルオロプロピルチオ基、3,3,3−トリフルオロプロピルチオ基、ノナフルオロブチルチオ基、ペルフルオロペンチルチオ基およびペルフルオロヘキシルチオ基が挙げられる。Examples of the C1-C6 alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, a tert-butylthio group, a pentylthio group, an isopentylthio group, and a neopentyl group. Ruthio group, isoamylthio group, 2-pentylthio group, 3-pentylthio group, 2-methylbutylthio group, hexylthio group, isohexylthio group, sec-hexylthio group, 3-methylpentylthio group and 4-methylpentylthio group Is mentioned.
The C1-C6 haloalkylthio group represents a group in which at least one hydrogen atom of the linear or branched C1-C6 alkylthio group is substituted with a halogen atom, and examples thereof include a fluoromethylthio group, a difluoromethylthio group, Trifluoromethylthio group, pentafluoroethylthio group, 2,2,2-trifluoroethylthio group, 2,2-difluoroethylthio group, heptafluoropropylthio group, 3,3,3-trifluoropropylthio group, Examples include 2,2-difluoropropylthio group, 3,3,3-trifluoropropylthio group, nonafluorobutylthio group, perfluoropentylthio group and perfluorohexylthio group.
C3−C6シクロアルキルオキシ基としては、例えば、シクロプロピルオキシ基、シクロブチルオキシ基、シクロペンチルオキシ基およびシクロヘキシルオキシ基が挙げられる。
C3−C6ハロシクロアルキルオキシ基とは、C3−C6シクロアルキルオキシ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、2−フルオロシクロプロピルオキシ基、2,2−ジフルオロシクロプロピルオキシ基、2−クロロ−2−フルオロシクロプロピルオキシ基、2,2−ジクロロシクロプロピルオキシ基、2,2−ジブロモシクロプロピルオキシ基、2,2−ジフルオロ−1−メチルシクロプロピルオキシ基、2,2−ジクロロ−1−メチルシクロプロピルオキシ基、2,2−ジブロモ−1−メチルシクロプロピルオキシ基、1−(トリフルオロメチル)シクロプロピルオキシ基、2,2,3,3−テトラフルオロシクロブチルオキシ基、2−クロロシクロヘキシルオキシ基、4,4−ジフルオロシクロヘキシルオキシ基および4−クロロシクロヘキシルオキシ基が挙げられる。
C3−C6シクロアルキルチオ基とは、例えば、シクロプロピルチオ基、シクロブチルチオ基、シクロペンチルチオ基およびシクロヘキシルチオ基が挙げられる。Examples of the C3-C6 cycloalkyloxy group include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, and a cyclohexyloxy group.
The C3-C6 halocycloalkyloxy group represents a group in which at least one hydrogen atom of the C3-C6 cycloalkyloxy group is substituted with a halogen atom, such as a 2-fluorocyclopropyloxy group, 2,2- Difluorocyclopropyloxy group, 2-chloro-2-fluorocyclopropyloxy group, 2,2-dichlorocyclopropyloxy group, 2,2-dibromocyclopropyloxy group, 2,2-difluoro-1-methylcyclopropyloxy group Group, 2,2-dichloro-1-methylcyclopropyloxy group, 2,2-dibromo-1-methylcyclopropyloxy group, 1- (trifluoromethyl) cyclopropyloxy group, 2,2,3,3- Tetrafluorocyclobutyloxy group, 2-chlorocyclohexyloxy group, 4,4-difluoro Black hexyloxy group and 4-chloro-cyclohexyloxy group.
Examples of the C3-C6 cycloalkylthio group include a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, and a cyclohexylthio group.
C2−C6アルケニルオキシ基としては、例えば、ビニルオキシ基、2−プロペニルオキシ基、2−ブテニルオキシ基、1−メチル−2−プロペニルオキシ基、3−ブテニルオキシ基、2−メチル−2−プロペニルオキシ基、2−ペンテニルオキシ基、3−ペンテニルオキシ基、4−ペンテニルオキシ基、1−メチル−3−ブテニルオキシ基、1,2−ジメチル−2−プロペニルオキシ基、1,1−ジメチル−2−プロペニルオキシ基、2−メチル−2−ブテニルオキシ基、3−メチル−2−ブテニルオキシ基、2−メチル−3−ブテニルオキシ基、3−メチル−3−ブテニルオキシ基、1−ビニル−2−プロペニルオキシ基および5−ヘキセニルオキシ基が挙げられる。
C2−C6ハロアルケニルオキシ基とは、C2−C6アルケニルオキシ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、1−フルオロビニルオキシ基、2−フルオロビニルオキシ基、3,3−ジフルオロ−2−プロペニルオキシ基、4,4,4−トリフルオロ−2−ブテニルオキシ基、3,4,4−トリフルオロ−3−ブテニルオキシ基、3,3−ジフルオロ−2−メチル−2−プロペニルオキシ基、ペルフルオロ−3−ブテニルオキシ基およびペルフルオロ−5−ヘキセニルオキシ基が挙げられる。
C2−C6アルキニルオキシ基としては、例えば、エチニルオキシ基、プロパルギルオキシ基、3−ブチン−2−イルオキシ基、2−ブチニルオキシ基、3−ブチニルオキシ基、2−メチル−3−ブチン−2−イルオキシ基、2−ペンチニルオキシ基、3−ペンチニルオキシ基、4−ペンチニルオキシ基および5−ヘキシニルオキシ基が挙げられる。
C2−C6ハロアルキニルオキシ基とは、C2−C6アルキニルオキシ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、ブロモエチニルオキシ基、3‐クロロ‐2‐プロピニルオキシ基、3‐ブロモ‐2‐プロピニルオキシ基、3‐ヨード‐2‐プロピニルオキシ基、5‐クロロ‐4‐ペンチニルオキシ基、3,3,3−トリフルオロ−1−プロピニルオキシ基、ペルフルオロ−2−ブチニルオキシ基、ペルフルオロ−3−ブチニルオキシ基、ペルフルオロ−2−ペンチニルオキシ基、ペルフルオロ−3−ペンチニルオキシ基、ペルフルオロ−4−ペンチニルオキシ基およびペルフルオロ−5‐ヘキシニルオキシ基が挙げられる。Examples of the C2-C6 alkenyloxy group include a vinyloxy group, 2-propenyloxy group, 2-butenyloxy group, 1-methyl-2-propenyloxy group, 3-butenyloxy group, 2-methyl-2-propenyloxy group, 2-pentenyloxy group, 3-pentenyloxy group, 4-pentenyloxy group, 1-methyl-3-butenyloxy group, 1,2-dimethyl-2-propenyloxy group, 1,1-dimethyl-2-propenyloxy group 2-methyl-2-butenyloxy group, 3-methyl-2-butenyloxy group, 2-methyl-3-butenyloxy group, 3-methyl-3-butenyloxy group, 1-vinyl-2-propenyloxy group and 5-hexenyl An oxy group is mentioned.
The C2-C6 haloalkenyloxy group represents a group in which at least one hydrogen atom of the C2-C6 alkenyloxy group is substituted with a halogen atom. 3,3-difluoro-2-propenyloxy group, 4,4,4-trifluoro-2-butenyloxy group, 3,4,4-trifluoro-3-butenyloxy group, 3,3-difluoro-2-methyl- Examples thereof include 2-propenyloxy group, perfluoro-3-butenyloxy group and perfluoro-5-hexenyloxy group.
Examples of the C2-C6 alkynyloxy group include ethynyloxy group, propargyloxy group, 3-butyn-2-yloxy group, 2-butynyloxy group, 3-butynyloxy group, and 2-methyl-3-butyn-2-yloxy group. 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group and 5-hexynyloxy group.
The C2-C6 haloalkynyloxy group represents a group in which at least one hydrogen atom of the C2-C6 alkynyloxy group is substituted with a halogen atom. 3-bromo-2-propynyloxy group, 3-iodo-2-propynyloxy group, 5-chloro-4-pentynyloxy group, 3,3,3-trifluoro-1-propynyloxy group, perfluoro-2 -Butynyloxy group, perfluoro-3-butynyloxy group, perfluoro-2-pentynyloxy group, perfluoro-3-pentynyloxy group, perfluoro-4-pentynyloxy group and perfluoro-5-hexynyloxy group.
C3−C6アルケニルチオ基としては、例えば、ビニルチオ基、2−プロペニルチオ基、2−ブテニルチオ基、1−メチル−2−プロペニルチオ基、3−ブテニルチオ基、2−メチル−2−プロペニルチオ基、2−ペンテニルチオ基、3−ペンテニルチオ基、4−ペンテニルチオ基、1−メチル−3−ブテニルチオ基、1,2−ジメチル−2−プロペニルチオ基、1,1−ジメチル−2−プロペニルチオ基、2−メチル−2−ブテニルチオ基、3−メチル−2−ブテニルチオ基、2−メチル−3−ブテニルチオ基、3−メチル−3−ブテニルチオ基、1−ビニル−2−プロペニルチオ基および5−ヘキセニルチオ基が挙げられる。
C3−C6ハロアルケニルチオ基とは、C3−C6アルケニルチオ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、1−フルオロビニルチオ基、2−フルオロビニルチオ基、3−クロロ−2−プロペニルチオ基、3−ブロモ−2−プロペニルチオ基、3,3−ジフルオロ−2−プロペニルチオ基、4,4,4−トリフルオロ−2−ブテニルチオ基、3,4,4−トリフルオロ−3−ブテニルチオ基、3,3−ジフルオロ−2−メチル−2−プロペニルチオ基、ペルフルオロ−3−ブテニルチオ基およびペルフルオロ−5−ヘキセニルチオ基が挙げられる。
C3−C6アルキニルチオ基としては、例えば、エチニルチオ基、プロパルギルチオ基、3−ブチン−2−イルチオ基、2−ブチニルチオ基、3−ブチニルチオ基、2−メチル−3−ブチン−2−イルチオ基、2−ペンチニルチオ基、3−ペンチニルチオ基、4−ペンチニルチオ基および5−ヘキシニルチオ基が挙げられる。
C3−C6ハロアルキニルチオ基とは、C3−C6アルキニルチオ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、ブロモエチニルチオ基、3‐クロロ‐2‐プロピニルチオ基、3‐ブロモ‐2‐プロピニルチオ基、3‐ヨード‐2‐プロピニルチオ基、5‐クロロ‐4‐ペンチニルチオ基、3,3,3−トリフルオロ−1−プロピニルチオ基、ペルフルオロ−2−ブチニルチオ基、ペルフルオロ−3−ブチニルチオ基、ペルフルオロ−2−ペンチニルチオ基、ペルフルオロ−3−ペンチニルチオ基、ペルフルオロ−4−ペンチニルチオ基およびペルフルオロ−5‐ヘキシニルチオ基が挙げられる。Examples of the C3-C6 alkenylthio group include a vinylthio group, a 2-propenylthio group, a 2-butenylthio group, a 1-methyl-2-propenylthio group, a 3-butenylthio group, a 2-methyl-2-propenylthio group, 2-pentenylthio group, 3-pentenylthio group, 4-pentenylthio group, 1-methyl-3-butenylthio group, 1,2-dimethyl-2-propenylthio group, 1,1-dimethyl-2-propenylthio group 2-methyl-2-butenylthio group, 3-methyl-2-butenylthio group, 2-methyl-3-butenylthio group, 3-methyl-3-butenylthio group, 1-vinyl-2-propenylthio group and 5-hexenyl A thio group is mentioned.
The C3-C6 haloalkenylthio group represents a group in which at least one hydrogen atom of the C3-C6 alkenylthio group is substituted with a halogen atom, such as a 1-fluorovinylthio group, a 2-fluorovinylthio group, 3-chloro-2-propenylthio group, 3-bromo-2-propenylthio group, 3,3-difluoro-2-propenylthio group, 4,4,4-trifluoro-2-butenylthio group, 3,4, Examples include 4-trifluoro-3-butenylthio group, 3,3-difluoro-2-methyl-2-propenylthio group, perfluoro-3-butenylthio group, and perfluoro-5-hexenylthio group.
Examples of the C3-C6 alkynylthio group include ethynylthio group, propargylthio group, 3-butyn-2-ylthio group, 2-butynylthio group, 3-butynylthio group, 2-methyl-3-butyn-2-ylthio group, Examples include 2-pentynylthio group, 3-pentynylthio group, 4-pentynylthio group, and 5-hexynylthio group.
The C3-C6 haloalkynylthio group represents a group in which at least one hydrogen atom of the C3-C6 alkynylthio group is substituted with a halogen atom, such as a bromoethynylthio group or a 3-chloro-2-propynylthio group. 3-bromo-2-propynylthio group, 3-iodo-2-propynylthio group, 5-chloro-4-pentynylthio group, 3,3,3-trifluoro-1-propynylthio group, perfluoro-2-butynylthio group Group, perfluoro-3-butynylthio group, perfluoro-2-pentynylthio group, perfluoro-3-pentynylthio group, perfluoro-4-pentynylthio group and perfluoro-5-hexynylthio group.
C2−C6アルキルカルボニル基とは、カルボニルの炭素も含めた合計の炭素数が2〜6であるアルキルカルボニル基であり、例えば、アセチル基、プロピオニル基、ブタノイル基、ペンタノイル基およびヘキサノイル基が挙げられる。
C2−C6ハロアルキルカルボニル基とは、C2−C6アルキルカルボニル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、トリクロロアセチル基、フルオロアセチル基、ジフルオロアセチル基、トリフルオロアセチル基、ペンタフルオロプロピオニル基、ペンタクロロプロピオニル基、ペンタブロモプロピオニル基、ペンタヨードプロピオニル基、3,3,3−トリクロロプロピオニル基、3,3,3−トリフルオロプロピオニル基、3,3,3−トリブロモプロピオニル基、3,3,3−トリヨードプロピオニル基、ヘプタフルオロブタノイル基、ヘプタクロロブタノイル基、ヘプタブロモブタノイル基、ヘプタヨードブタノイル基、4,4,4−トリフルオロブタノイル基、4,4,4−トリクロロブタノイル基、4,4,4−トリブロモブタノイル基、4,4,4−トリヨードブタノイル基、ノナフルオロペンタノイル基、ノナクロロペンタノイル基、ノナブロモペンタノイル基、ノナヨードペンタノイル基およびペルフルオロヘキサノイル基が挙げられる。
C2−C6アルキルカルボニルオキシ基とは、カルボニルの炭素も含めた合計の炭素数が2〜6であるアルキルカルボニルオキシ基を表し、例えば、アセトキシ基、プロピオニルオキシ基、ブタノイルオキシ基、ペンタノイルオキシ基およびヘキサノイルオキシ基が挙げられる。
C2−C6アルキルカルボニルチオ基とは、カルボニルの炭素も含めた合計の炭素数が2〜6である基を表し、例えば、アセチルチオ基、プロピオニルチオ基、ブタノイルチオ基、ペンタノイルチオ基およびヘキサノイルチオ基が挙げられる。
C2−C6アルコキシカルボニル基とは、アルコキシ部分とカルボニルの合計の炭素原子数が2〜6である基を表し、例えば、メトキシカルボニル基、エトキシカルボニル基、プロポキシカルボニル基、イソプロポキシカルボニル基、ブトキシカルボニル基、イソブトキシカルボニル基、sec−ブトキシカルボニル基、tert−ブトキシカルボニル基、ペンチルオキシカルボニル基、イソアミルオキシカルボニル基、ネオペンチルオキシカルボニル基、2−ペンチルオキシカルボニル基、3−ペンチルオキシカルボニル基および2−メチルブトキシカルボニル基が挙げられる。The C2-C6 alkylcarbonyl group is an alkylcarbonyl group having 2 to 6 carbon atoms in total including carbon of the carbonyl, and examples thereof include an acetyl group, a propionyl group, a butanoyl group, a pentanoyl group, and a hexanoyl group. .
The C2-C6 haloalkylcarbonyl group represents a group in which at least one hydrogen atom of the C2-C6 alkylcarbonyl group is substituted with a halogen atom. For example, a trichloroacetyl group, a fluoroacetyl group, a difluoroacetyl group, a trifluoroacetyl group Group, pentafluoropropionyl group, pentachloropropionyl group, pentabromopropionyl group, pentaiodopropionyl group, 3,3,3-trichloropropionyl group, 3,3,3-trifluoropropionyl group, 3,3,3-tri Bromopropionyl group, 3,3,3-triiodopropionyl group, heptafluorobutanoyl group, heptachlorobutanoyl group, heptabromobutanoyl group, heptaiodobutanoyl group, 4,4,4-trifluorobutanoyl group 4,4,4-trichloro Tanoyl group, 4,4,4-tribromobutanoyl group, 4,4,4-triiodobutanoyl group, nonafluoropentanoyl group, nonachloropentanoyl group, nonabromopentanoyl group, nonaiodopentanoyl group And perfluorohexanoyl groups.
The C2-C6 alkylcarbonyloxy group represents an alkylcarbonyloxy group having 2 to 6 carbon atoms in total including carbon of the carbonyl, such as an acetoxy group, a propionyloxy group, a butanoyloxy group, a pentanoyloxy group. Groups and hexanoyloxy groups.
The C2-C6 alkylcarbonylthio group represents a group having 2 to 6 carbon atoms in total including the carbon of the carbonyl. For example, acetylthio group, propionylthio group, butanoylthio group, pentanoylthio group and hexanoylthio group Groups.
C2-C6 alkoxycarbonyl group represents a group having 2 to 6 carbon atoms in total of the alkoxy moiety and carbonyl, such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbonyl group, butoxycarbonyl. Group, isobutoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, pentyloxycarbonyl group, isoamyloxycarbonyl group, neopentyloxycarbonyl group, 2-pentyloxycarbonyl group, 3-pentyloxycarbonyl group and 2 -A methyl butoxycarbonyl group is mentioned.
C1−C6アルキルスルホニル基としては、例えば、メチルスルホニル基、エチルスルホニル基、プロピルスルホニル基、イソプロピルスルホニル基、ブチルスルホニル基、イソブチルスルホニル基、sec−ブチルスルホニル基、tert−ブチルスルホニル基、ペンチルスルホニル基、イソペンチルスルホニル基、ネオペンチルスルホニル基、イソアミルスルホニル基、2−ペンチルスルホニル基、3−ペンチルスルホニル基、2−メチルブチルスルホニル基、ヘキシルスルホニル基、イソヘキシルスルホニル基、sec−ヘキシルスルホニル基、3−メチルペンチルスルホニル基および4−メチルペンチルスルホニル基が挙げられる。
C1−C6ハロアルキルスルホニル基とは、C1−C6アルキルスルホニル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、フルオロメチルスルホニル基、ブロモジフルオロメチルスルホニル基、ジフルオロメチルスルホニル基、トリフルオロメチルスルホニル基、トリクロロメチルスルホニル基、トリブロモメチルスルホニル基、トリヨードメチルスルホニル基、クロロフルオロメチルスルホニル基、ペンタフルオロエチルスルホニル基、ペンタクロロエチルスルホニル基、ペンタブロモエチルスルホニル基、ペンタヨードエチルスルホニル基、2,2,2−トリクロロエチルスルホニル基、2,2,2−トリフルオロエチルスルホニル基、2,2,2−トリフルオロエチルスルホニル基、2,2,2−トリブロモエチルスルホニル基、2,2,2−トリヨードエチルスルホニル基、2,2−ジフルオロエチルスルホニル基、ヘプタフルオロプロピルスルホニル基、ヘプタクロロプロピルスルホニル基、ヘプタブロモプロピルスルホニル基、ヘプタヨードプロピルスルホニル基、3,3,3−トリフルオロプロピルスルホニル基、3,3,3−トリクロロプロピルスルホニル基、3,3,3−トリブロモプロピルスルホニル基、3,3,3−トリヨードプロピルスルホニル基、2,2−ジフルオロプロピルスルホニル基、3,3,3−トリフルオロプロピルスルホニル基、ノナフルオロブチルスルホニル基、ノナクロロブチルスルホニル基、ノナブロモブチルスルホニル基、ノナヨードブチルスルホニル基、ペルフルオロペンチルスルホニル基、ペルクロロペンチルスルホニル基、ペルブロモペンチルスルホニル基、ペルフルオロヘキシルスルホニル基、ペルクロロヘキシルスルホニル基、ペルブロモヘキシルスルホニル基およびペルヨードヘキシルスルホニル基が挙げられる。Examples of the C1-C6 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, an isobutylsulfonyl group, a sec-butylsulfonyl group, a tert-butylsulfonyl group, and a pentylsulfonyl group. , Isopentylsulfonyl group, neopentylsulfonyl group, isoamylsulfonyl group, 2-pentylsulfonyl group, 3-pentylsulfonyl group, 2-methylbutylsulfonyl group, hexylsulfonyl group, isohexylsulfonyl group, sec-hexylsulfonyl group, 3 -A methyl pentyl sulfonyl group and a 4-methyl pentyl sulfonyl group are mentioned.
The C1-C6 haloalkylsulfonyl group represents a group in which at least one hydrogen atom of the C1-C6 alkylsulfonyl group is substituted with a halogen atom. For example, a fluoromethylsulfonyl group, a bromodifluoromethylsulfonyl group, a difluoromethylsulfonyl group , Trifluoromethylsulfonyl group, trichloromethylsulfonyl group, tribromomethylsulfonyl group, triiodomethylsulfonyl group, chlorofluoromethylsulfonyl group, pentafluoroethylsulfonyl group, pentachloroethylsulfonyl group, pentabromoethylsulfonyl group, pentaiodo Ethylsulfonyl group, 2,2,2-trichloroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2,2,2- Ribromoethylsulfonyl group, 2,2,2-triiodoethylsulfonyl group, 2,2-difluoroethylsulfonyl group, heptafluoropropylsulfonyl group, heptachloropropylsulfonyl group, heptabromopropylsulfonyl group, heptaiodopropylsulfonyl group 3,3,3-trifluoropropylsulfonyl group, 3,3,3-trichloropropylsulfonyl group, 3,3,3-tribromopropylsulfonyl group, 3,3,3-triiodopropylsulfonyl group, 2, 2-difluoropropylsulfonyl group, 3,3,3-trifluoropropylsulfonyl group, nonafluorobutylsulfonyl group, nonachlorobutylsulfonyl group, nonabromobutylsulfonyl group, nonaiodobutylsulfonyl group, perfluoropentylsulfonyl group Perchlorethylene pentylsulfonyl group, per bromo pentylsulfonyl group, perfluorohexyl sulfonyl group, perchlorethylene hexylsulfonyl group, and a perfluoroalkyl bromohexyl sulfonyl groups and perfluoroalkyl-iodo hexyl sulfonyl group.
C1−C6アルキルスルフィニル基としては、例えば、メチルスルフィニル基、エチルスルフィニル基、プロピルスルフィニル基、イソプロピルスルフィニル基、ブチルスルフィニル基、イソブチルスルフィニル基、sec−ブチルスルフィニル基、tert−ブチルスルフィニル基、ペンチルスルフィニル基、イソペンチルスルフィニル基、ネオペンチルスルフィニル基、イソアミルスルフィニル基、2−ペンチルスルフィニル基、3−ペンチルスルフィニル基、2−メチルブチルスルフィニル基、ヘキシルスルフィニル基、イソヘキシルスルフィニル基、sec−ヘキシルスルフィニル基、3−メチルペンチルスルフィニル基および4−メチルペンチルスルフィニル基が挙げられる。
C1−C6ハロアルキルスルフィニル基とは、C1−C6アルキルスルフィニル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、モノフルオロメチルスルフィニル基、ジフルオロメチルスルフィニル基、トリフルオロメチルスルフィニル基、トリクロロメチルスルフィニル基、ペンタフルオロエチルスルフィニル基、2,2,2−トリフルオロエチルスルフィニル基、2,2−ジフルオロエチルスルフィニル基、ヘプタフルオロプロピルスルフィニル基、3,3,3−トリフルオロプロピルスルフィニル基、2,2−ジフルオロプロピルスルフィニル基、3,3,3−トリフルオロプロピルスルフィニル基、ノナフルオロブチルスルフィニル基、ペルフルオロペンチルスルフィニル基およびペルフルオロヘキシルスルフィニル基が挙げられる。Examples of the C1-C6 alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutylsulfinyl group, a sec-butylsulfinyl group, a tert-butylsulfinyl group, and a pentylsulfinyl group. , Isopentylsulfinyl group, neopentylsulfinyl group, isoamylsulfinyl group, 2-pentylsulfinyl group, 3-pentylsulfinyl group, 2-methylbutylsulfinyl group, hexylsulfinyl group, isohexylsulfinyl group, sec-hexylsulfinyl group, 3 -Methylpentylsulfinyl group and 4-methylpentylsulfinyl group are mentioned.
The C1-C6 haloalkylsulfinyl group represents a group in which at least one hydrogen atom of the C1-C6 alkylsulfinyl group is substituted with a halogen atom. Group, trichloromethylsulfinyl group, pentafluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2,2-difluoroethylsulfinyl group, heptafluoropropylsulfinyl group, 3,3,3-trifluoropropylsulfinyl group Group, 2,2-difluoropropylsulfinyl group, 3,3,3-trifluoropropylsulfinyl group, nonafluorobutylsulfinyl group, perfluoropentylsulfinyl group and perfluorohexene Shirusurufiniru group, and the like.
C1−C6アルキル基を有していてもよいアミノ基とは、アミノ基の有する1または2の水素原子がC1−C6アルキル基で置換されていてもよいアミノ基であり、ジアルキルアミノ基の場合、窒素原子上のアルキル基は互いに同一でも相異なっていてもよい。C1−C6アルキル基を有していてもよいアミノ基としては、例えば、アミノ基、N−メチルアミノ基、N,N−ジメチルアミノ基、N−エチルアミノ基、N−エチル−N−メチルアミノ基、N,N−ジエチルアミノ基、N−プロピルアミノ基、N−イソプロピルアミノ基、N−プロピル−N−メチルアミノ基、N,N−ジプロピルアミノ基、N,N−ジイソプロピルアミノ基、N−ブチルアミノ基、N−ブチル−N−メチルアミノ基、N,N−ジブチルアミノ基、N−ペンチルアミノ基、N−ペンチル−N−メチルアミノ基およびN−ヘキシルアミノ基が挙げられる。
C1−C6アルキル基を有していてもよいアミノカルボニル基とは、アミノカルボニル基が有する1または2の水素原子が、C1−C6アルキル基で置換されていてもよいアミノカルボニル基であり、ジアルキルアミノカルボニル基の場合、窒素原子上のアルキル基は互いに同一でも相異なっていてもよい。1−C6アルキル基を有していてもよいアミノカルボニル基としては、例えば、アミノカルボニル基、N−メチルアミノカルボニル基、N−エチルアミノカルボニル基、N−プロピルアミノカルボニル基、N−イソプロピルアミノカルボニル基、N−ブチルアミノカルボニル基およびN−ペンチルアミノカルボニル基が挙げられる。
C1−C6アルキル基を有していてもよいアミノスルホニル基とは、アミノスルホニル基が有する1または2の水素原子が、C1−C6アルキル基で置換されていてもよいアミノスルホニル基であり、ジアルキルアミノスルホニル基の場合、窒素原子上のアルキル基は互いに同一でも相異なっていてもよい。C1−C6アルキル基で有していてもよいアミノスルホニル基としては、例えば、アミノスルホニル基、N−メチルアミノスルホニル基、N−エチルアミノスルホニル基、N−プロピルアミノスルホニル基、N−イソプロピルアミノスルホニル基、N−ブチルアミノスルホニル基、N−ペンチルアミノスルホニル基およびN−ヘキシルアミノスルホニル基が挙げられる。The amino group optionally having a C1-C6 alkyl group is an amino group in which one or two hydrogen atoms of the amino group may be substituted with a C1-C6 alkyl group, and in the case of a dialkylamino group The alkyl groups on the nitrogen atom may be the same as or different from each other. Examples of the amino group optionally having a C1-C6 alkyl group include an amino group, an N-methylamino group, an N, N-dimethylamino group, an N-ethylamino group, and an N-ethyl-N-methylamino group. Group, N, N-diethylamino group, N-propylamino group, N-isopropylamino group, N-propyl-N-methylamino group, N, N-dipropylamino group, N, N-diisopropylamino group, N- Examples include a butylamino group, an N-butyl-N-methylamino group, an N, N-dibutylamino group, an N-pentylamino group, an N-pentyl-N-methylamino group, and an N-hexylamino group.
The aminocarbonyl group which may have a C1-C6 alkyl group is an aminocarbonyl group in which one or two hydrogen atoms of the aminocarbonyl group may be substituted with a C1-C6 alkyl group. In the case of an aminocarbonyl group, the alkyl groups on the nitrogen atom may be the same or different from each other. Examples of the aminocarbonyl group optionally having 1-C6 alkyl group include aminocarbonyl group, N-methylaminocarbonyl group, N-ethylaminocarbonyl group, N-propylaminocarbonyl group, N-isopropylaminocarbonyl. Group, N-butylaminocarbonyl group and N-pentylaminocarbonyl group.
The aminosulfonyl group which may have a C1-C6 alkyl group is an aminosulfonyl group in which one or two hydrogen atoms of the aminosulfonyl group may be substituted with a C1-C6 alkyl group, and a dialkyl In the case of an aminosulfonyl group, the alkyl groups on the nitrogen atom may be the same as or different from each other. Examples of the aminosulfonyl group optionally having a C1-C6 alkyl group include an aminosulfonyl group, an N-methylaminosulfonyl group, an N-ethylaminosulfonyl group, an N-propylaminosulfonyl group, and an N-isopropylaminosulfonyl group. Group, N-butylaminosulfonyl group, N-pentylaminosulfonyl group and N-hexylaminosulfonyl group.
C1−C4アルコキシ基としては、例えば、メトキシ基、エトキシ基、プロポキシ基、イソプロポキシ基、ブトキシ基、イソブトキシ基、sec−ブトキシ基およびtert−ブトキシ基が挙げられる。
C1−C4ハロアルコキシ基とは、C1−C4アルコキシ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、トリフルオロメトキシ基、トリクロロメトキシ基、クロロメトキシ基、ジクロロメトキシ基、フルオロメトキシ基、ジフルオロメトキシ基、ペンタフルオロエトキシ基、2,2,2−トリフルオロエトキシ基、2−フルオロエトキシ基、2,2−ジフルオロエトキシ基ヘプタフルオロプロポキシ基、3,3,3−トリフルオロプロポキン基、2−フルオロプロポキシ基、3−フルオロプロポキシ基、2,2−ジフルオロプロポキシ基、2,3−ジフルオロプロポキシ基、3,3,3−トリフルオロプロポキシ基およびノナフルオロブトキシ基が挙げられる。
C1−C4アルキルチオ基としては、例えば、メチルチオ基、エチルチオ基、プロピルチオ基、イソプロピルチオ基、ブチルチオ基、イソブチルチオ基、sec−ブチルチオ基およびtert−ブチルチオ基が挙げられる。
C1−C4ハロアルキルチオ基とは、C1−C4アルキルチオ基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、トリフルオロメチルチオ基、トリクロロメチルチオ基、クロロメチルチオ基、ジクロロメチルチオ基、フルオロメチルチオ基、ジフルオロメチルチオ基、ペンタフルオロエチルチオ基、2,2,2−トリクロロエチルチオ基、2,2,2−トリフルオロエチルチオ基、2−フルオロエチルチオ基、2,2−ジフルオロエチルチオ基、ヘプタフルオロプロピルチオ基、3,3,3−トリフルオロプロピルチオ基、2−フルオロプロピルチオ基、3−フルオロプロピルチオ基、2,2−ジフルオロプロピルチオ基、2,3−ジフルオロプロピルチオ基、3,3,3−トリフルオロプロピルチオ基およびノナフルオロブチルチオ基が挙げられる。Examples of the C1-C4 alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, and a tert-butoxy group.
The C1-C4 haloalkoxy group represents a group in which at least one hydrogen atom of the C1-C4 alkoxy group is substituted with a halogen atom. , Fluoromethoxy group, difluoromethoxy group, pentafluoroethoxy group, 2,2,2-trifluoroethoxy group, 2-fluoroethoxy group, 2,2-difluoroethoxy group, heptafluoropropoxy group, 3,3,3-tri Fluoropropoxy group, 2-fluoropropoxy group, 3-fluoropropoxy group, 2,2-difluoropropoxy group, 2,3-difluoropropoxy group, 3,3,3-trifluoropropoxy group and nonafluorobutoxy group It is done.
Examples of the C1-C4 alkylthio group include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, a sec-butylthio group, and a tert-butylthio group.
The C1-C4 haloalkylthio group represents a group in which at least one hydrogen atom of the C1-C4 alkylthio group is substituted with a halogen atom, such as a trifluoromethylthio group, a trichloromethylthio group, a chloromethylthio group, a dichloromethylthio group. , Fluoromethylthio group, difluoromethylthio group, pentafluoroethylthio group, 2,2,2-trichloroethylthio group, 2,2,2-trifluoroethylthio group, 2-fluoroethylthio group, 2,2-difluoro Ethylthio group, heptafluoropropylthio group, 3,3,3-trifluoropropylthio group, 2-fluoropropylthio group, 3-fluoropropylthio group, 2,2-difluoropropylthio group, 2,3-difluoro Propylthio group, 3,3,3-trifluoropropylthio group and It includes nonafluorobutyl thio group.
C1−C4アルキルスルホニル基としては、例えば、メチルスルホニル基、エチルスルホニル基、プロピルスルホニル基、イソプロピルスルホニル基、ブチルスルホニル基、イソブチルスルホニル基、sec−ブチルスルホニル基およびtert−ブチルスルホニル基が挙げられる。
C1−C4ハロアルキルスルホニル基とは、C1−C4アルキルスルホニル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、トリフルオロメチルスルホニル基、トリクロロメチルスルホニル基、クロロメチルスルホニル基、ジクロロメチルスルホニル基、フルオロメチルスルホニル基、ジフルオロメチルスルホニル基、ペンタフルオロエチルスルホニル基、2,2,2−トリフルオロエチルスルホニル基、2−フルオロエチルスルホニル基、2,2−ジフルオロエチルスルホニル基、ヘプタフルオロプロピルスルホニル基、3,3,3−トリフルオロプロピルスルホニル基、2−フルオロプロピルスルホニル基、3−フルオロプロピルスルホニル基、2,2−ジフルオロプロピルスルホニル基、2,3−ジフルオロプロピルスルホニル基、3,3,3−トリフルオロプロピルスルホニル基およびノナフルオロブチルスルホニル基が挙げられる。Examples of the C1-C4 alkylsulfonyl group include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, an isobutylsulfonyl group, a sec-butylsulfonyl group, and a tert-butylsulfonyl group.
The C1-C4 haloalkylsulfonyl group represents a group in which at least one hydrogen atom of the C1-C4 alkylsulfonyl group is substituted with a halogen atom, such as a trifluoromethylsulfonyl group, a trichloromethylsulfonyl group, or a chloromethylsulfonyl group. Dichloromethylsulfonyl group, fluoromethylsulfonyl group, difluoromethylsulfonyl group, pentafluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2-fluoroethylsulfonyl group, 2,2-difluoroethylsulfonyl group, Heptafluoropropylsulfonyl group, 3,3,3-trifluoropropylsulfonyl group, 2-fluoropropylsulfonyl group, 3-fluoropropylsulfonyl group, 2,2-difluoropropylsulfonyl group, 2,3-di Le Oro propylsulfonyl group, 3,3,3-trifluoropropyl sulfonyl group and nonafluorobutylsulfonyl group.
C3−C9トリアルキルシリル基としては、例えば、トリメチルシリル基、tert−ブチルジメチルシリル基、トリエチルシリル基、イソプロピルジメチルシリル基およびトリイソプロピルシリル基が挙げられる。 Examples of the C3-C9 trialkylsilyl group include a trimethylsilyl group, a tert-butyldimethylsilyl group, a triethylsilyl group, an isopropyldimethylsilyl group, and a triisopropylsilyl group.
C5−C14トリアルキルシリルエチニル基とは、トリアルキルシリル基が結合したエチニル基を表し、エチニル基の炭素も含めた合計の炭素原子数が5〜14であり、シリル基上の3つのアルキル基は同一または相異なっていてもよく、例えば、トリメチルシリルエチニル基、tert−ブチルジメチルシリルエチニル基、トリエチルシリルエチニル基、イソプロピルジメチルシリルエチニル基、トリイソプロピルシリルエチニル基、トリ(tert−ブチル)シリルエチニル基およびトリブチルシリルエチニル基が挙げられる。
C1−C4アルキルスルフィニル基としては、例えば、メチルスルフィニル基、エチルスルフィニル基、プロピルスルフィニル基、イソプロピルスルフィニル基、ブチルスルフィニル基、イソブチルスルフィニル基、sec−ブチルスルフィニル基およびtert−ブチルスルフィニル基が挙げられる。
C1−C4ハロアルキルスルフィニル基とは、C1−C4アルキルスルフィニル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、トリフルオロメチルスルフィニル基、トリクロロメチルスルフィニル基、クロロメチルスルフィニル基、ジクロロメチルスルフィニル基、フルオロメチルスルフィニル基、ジフルオロメチルスルフィニル基、ペンタフルオロエチルスルフィニル基、2,2,2−トリフルオロエチルスルフィニル基、2−フルオロエチルスルフィニル基、2,2−ジフルオロエチルスルフィニル基、ヘプタフルオロプロピルスルフィニル基、3,3,3−トリフルオロプロピルスルフィニル基、2−フルオロプロピルスルフィニル基、3−フルオロプロピルスルフィニル基、2,2−ジフルオロプロピルスルフィニル基、2,3−ジフルオロプロピルスルフィニル基およびノナフルオロブチルスルフィニル基が挙げられる。The C5-C14 trialkylsilylethynyl group represents an ethynyl group to which a trialkylsilyl group is bonded, the total number of carbon atoms including the carbon of the ethynyl group is 5 to 14, and three alkyl groups on the silyl group May be the same or different, for example, trimethylsilylethynyl group, tert-butyldimethylsilylethynyl group, triethylsilylethynyl group, isopropyldimethylsilylethynyl group, triisopropylsilylethynyl group, tri (tert-butyl) silylethynyl group And tributylsilylethynyl group.
Examples of the C1-C4 alkylsulfinyl group include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, an isobutylsulfinyl group, a sec-butylsulfinyl group, and a tert-butylsulfinyl group.
The C1-C4 haloalkylsulfinyl group represents a group in which at least one hydrogen atom of the C1-C4 alkylsulfinyl group is substituted with a halogen atom, such as a trifluoromethylsulfinyl group, a trichloromethylsulfinyl group, or a chloromethylsulfinyl group. Dichloromethylsulfinyl group, fluoromethylsulfinyl group, difluoromethylsulfinyl group, pentafluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2-fluoroethylsulfinyl group, 2,2-difluoroethylsulfinyl group, Heptafluoropropylsulfinyl group, 3,3,3-trifluoropropylsulfinyl group, 2-fluoropropylsulfinyl group, 3-fluoropropylsulfinyl group, 2,2-difluoro B Pils sulfinyl group, 2,3-difluoro-propyl sulfinyl group, and a nonafluorobutyl sulfinyl group.
C2−C5アルコキシアルキル基とは、アルコキシ部分とアルキル部分との合計の炭素原子数が2〜5である基を表し、例えば、メトキシメチル基、エトキシメチル基、プロポキシメチル基、イソプロポキシメチル基、ブトキシメチル基、イソブトキシメチル基、sec−ブトキシメチル基、1−メトキシエチル基、2−メトキシエチル基、2−エトキシエチル基、2−プロポキシエチル基、2−イソプロポキシエチル基、2−ブトキシエチル基、3−メトキシプロピル基、3−エトキシプロピル基および3−メトキシブチル基があげられる。
C2−C5アルキルチオアルキル基は、アルキルチオ部分とアルキル部分との合計の炭素原子数が2〜5であり、直鎖状もしくは分枝状のいずれでもよく、例えば、メトキシメチル基、エトキシメチル基、プロポキシメチル基、イソプロポキシメチル基、ブトキシメチル基、イソブトキシメチル基、sec−ブトキシメチル基、1−メトキシエチル基、2−メトキシエチル基、2−エトキシエチル基、2−プロポキシエチル基、2−イソプロポキシエチル基、2−ブトキシエチル基、3−メトキシプロピル基、3−エトキシプロピル基または3−メトキシブチル基があげられる。The C2-C5 alkoxyalkyl group represents a group having 2 to 5 carbon atoms in total of an alkoxy moiety and an alkyl moiety, such as a methoxymethyl group, an ethoxymethyl group, a propoxymethyl group, an isopropoxymethyl group, Butoxymethyl group, isobutoxymethyl group, sec-butoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propoxyethyl group, 2-isopropoxyethyl group, 2-butoxyethyl Group, 3-methoxypropyl group, 3-ethoxypropyl group and 3-methoxybutyl group.
The C2-C5 alkylthioalkyl group has 2 to 5 carbon atoms in total of the alkylthio moiety and the alkyl moiety, and may be linear or branched. For example, a methoxymethyl group, an ethoxymethyl group, a propoxy group Methyl group, isopropoxymethyl group, butoxymethyl group, isobutoxymethyl group, sec-butoxymethyl group, 1-methoxyethyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2-propoxyethyl group, 2-iso Examples thereof include a propoxyethyl group, a 2-butoxyethyl group, a 3-methoxypropyl group, a 3-ethoxypropyl group, and a 3-methoxybutyl group.
C1−C3ハロアルキル基とは、C1−C3アルキル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、フルオロメチル基、クロロメチル基、ジクロロメチル基、ジフルオロメチル基、トリフルオロメチル基、トリクロロメチル基、トリブロモメチル基、クロロフルオロメチル基、ジクロロフルオロメチル基、2,2,2−トリフルオロエチル基、2,2,2−トリクロロエチル基、ペンタフルオロエチル基、クロロジフルオロメチル基、2,2−ジフルオロエチル基、2−クロロ−2−フルオロエチル基、2−クロロ−2,2−ジフルオロエチル基、2,2−ジクロロ−2−フルオロエチル基、2−フルオロプロピル基、3−フルオロプロピル基、2,2−ジフルオロプロピル基、および3,3,3−トリフルオロプロピル基が挙げられる。
C2−C3アルケニル基としては、ビニル基、1−プロペニル基、イソプロペニル基および2−プロペニル基が挙げられる。
C2−C3ハロアルケニル基とは、C2−3アルケニル基が有する少なくとも1の水素原子がハロゲン原子で置換された基を表し、例えば、2−クロロビニル基、2−ブロモビニル基、2−ヨ−ドビニル基、3−クロロ−2−プロペニル基、3−ブロモ−2−プロペニル基、1−クロロメチルビニル基、2−ブロモ−1−メチルビニル基、1−トリフルオロメチルビニル基、3,3,3−トリクロロ−1−プロペニル基、3−ブロモ−3,3−ジフルオロ−1−プロペニル基、2,3,3,3−テトラクロロ−1−プロペニル基、1−トリフルオロメチル−2,2−ジフルオロビニル基、2−クロロ−2−プロペニル基、3,3−ジフルオロ−2−プロペニル基、2,3,3−トリクロロ−2−プロペニル基、3,3−ジクロロ−2−プロペニル基、3,3−ジブロモ−2−プロペニル基および3−フルオロ−3−クロロ−2−プロペニル基が挙げられる。
C1−C3アルコキシ基としては、メトキシ基、エトキシ基、プロポキシ基およびイソプロポキシ基が挙げられる。The C1-C3 haloalkyl group represents a group in which at least one hydrogen atom of the C1-C3 alkyl group is substituted with a halogen atom. For example, a fluoromethyl group, a chloromethyl group, a dichloromethyl group, a difluoromethyl group, a trimethyl group, Fluoromethyl group, trichloromethyl group, tribromomethyl group, chlorofluoromethyl group, dichlorofluoromethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, chloro Difluoromethyl group, 2,2-difluoroethyl group, 2-chloro-2-fluoroethyl group, 2-chloro-2,2-difluoroethyl group, 2,2-dichloro-2-fluoroethyl group, 2-fluoropropyl Group, 3-fluoropropyl group, 2,2-difluoropropyl group, and 3,3,3-tri Ruoropuropiru group, and the like.
C2-C3 alkenyl groups include vinyl, 1-propenyl, isopropenyl and 2-propenyl groups.
The C2-C3 haloalkenyl group represents a group in which at least one hydrogen atom of the C2-3 alkenyl group is substituted with a halogen atom, such as a 2-chlorovinyl group, 2-bromovinyl group, 2-iodovinyl. Group, 3-chloro-2-propenyl group, 3-bromo-2-propenyl group, 1-chloromethylvinyl group, 2-bromo-1-methylvinyl group, 1-trifluoromethylvinyl group, 3, 3, 3 -Trichloro-1-propenyl group, 3-bromo-3,3-difluoro-1-propenyl group, 2,3,3,3-tetrachloro-1-propenyl group, 1-trifluoromethyl-2,2-difluoro Vinyl group, 2-chloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,3,3-trichloro-2-propenyl group, 3,3-dichloro-2-propene Group, include 3,3-dibromo-2-propenyl group and 3-fluoro-3-chloro-2-propenyl group.
C1-C3 alkoxy groups include methoxy, ethoxy, propoxy and isopropoxy groups.
本発明化合物の態様としては、例えば式(1)における置換基が以下のものである化合物が挙げられる。
EがE11であるテトラゾリノン化合物。EがE12であるテトラゾリノン化合物。
EがE13であるテトラゾリノン化合物。EがE14であるテトラゾリノン化合物。
EがE15であるテトラゾリノン化合物。EがE16であるテトラゾリノン化合物。
EがE17であるテトラゾリノン化合物。EがE18であるテトラゾリノン化合物。
EがE19であるテトラゾリノン化合物。EがE20であるテトラゾリノン化合物。
EがE21であるテトラゾリノン化合物。EがE22であるテトラゾリノン化合物。
EがE23であるテトラゾリノン化合物。EがE24であるテトラゾリノン化合物。
EがE25であるテトラゾリノン化合物。EがE26であるテトラゾリノン化合物。
EがE27であるテトラゾリノン化合物。EがE28であるテトラゾリノン化合物。
EがE29であるテトラゾリノン化合物。EがE30であるテトラゾリノン化合物。
EがE31であるテトラゾリノン化合物。EがE32であるテトラゾリノン化合物。
EがE33であるテトラゾリノン化合物。EがE34であるテトラゾリノン化合物。
EがE35であるテトラゾリノン化合物。EがE36であるテトラゾリノン化合物。
EがE37であるテトラゾリノン化合物。EがE38であるテトラゾリノン化合物。
EがE39であるテトラゾリノン化合物。EがE40であるテトラゾリノン化合物。
EがE41であるテトラゾリノン化合物。EがE42であるテトラゾリノン化合物。
EがE43であるテトラゾリノン化合物。EがE44であるテトラゾリノン化合物。
EがE45であるテトラゾリノン化合物。EがE46であるテトラゾリノン化合物。
EがE50であるテトラゾリノン化合物。EがE51であるテトラゾリノン化合物。
EがE52であるテトラゾリノン化合物。EがE53であるテトラゾリノン化合物。
EがE54であるテトラゾリノン化合物。EがE55であるテトラゾリノン化合物。
EがE56であるテトラゾリノン化合物。EがE57であるテトラゾリノン化合物。
EがE58であるテトラゾリノン化合物。EがE59であるテトラゾリノン化合物。
EがE60であるテトラゾリノン化合物。EがE61であるテトラゾリノン化合物。
EがE62であるテトラゾリノン化合物。EがE63であるテトラゾリノン化合物。
EがE64であるテトラゾリノン化合物。EがE65であるテトラゾリノン化合物。As an aspect of this invention compound, the compound whose substituent in Formula (1) is the following is mentioned, for example.
A tetrazolinone compound in which E is E11. A tetrazolinone compound in which E is E12.
A tetrazolinone compound in which E is E13. A tetrazolinone compound in which E is E14.
A tetrazolinone compound in which E is E15. A tetrazolinone compound in which E is E16.
A tetrazolinone compound in which E is E17. A tetrazolinone compound in which E is E18.
A tetrazolinone compound in which E is E19. A tetrazolinone compound in which E is E20.
A tetrazolinone compound in which E is E21. A tetrazolinone compound in which E is E22.
A tetrazolinone compound in which E is E23. A tetrazolinone compound in which E is E24.
A tetrazolinone compound in which E is E25. A tetrazolinone compound in which E is E26.
A tetrazolinone compound in which E is E27. A tetrazolinone compound in which E is E28.
A tetrazolinone compound in which E is E29. A tetrazolinone compound in which E is E30.
A tetrazolinone compound in which E is E31. A tetrazolinone compound in which E is E32.
A tetrazolinone compound in which E is E33. A tetrazolinone compound in which E is E34.
A tetrazolinone compound in which E is E35. A tetrazolinone compound in which E is E36.
A tetrazolinone compound in which E is E37. A tetrazolinone compound in which E is E38.
A tetrazolinone compound in which E is E39. A tetrazolinone compound in which E is E40.
A tetrazolinone compound in which E is E41. A tetrazolinone compound in which E is E42.
A tetrazolinone compound in which E is E43. A tetrazolinone compound in which E is E44.
A tetrazolinone compound in which E is E45. A tetrazolinone compound in which E is E46.
A tetrazolinone compound in which E is E50. A tetrazolinone compound in which E is E51.
A tetrazolinone compound in which E is E52. A tetrazolinone compound in which E is E53.
A tetrazolinone compound in which E is E54. A tetrazolinone compound in which E is E55.
A tetrazolinone compound in which E is E56. A tetrazolinone compound in which E is E57.
A tetrazolinone compound in which E is E58. A tetrazolinone compound in which E is E59.
A tetrazolinone compound in which E is E60. A tetrazolinone compound in which E is E61.
A tetrazolinone compound in which E is E62. A tetrazolinone compound in which E is E63.
A tetrazolinone compound in which E is E64. A tetrazolinone compound in which E is E65.
QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE11であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE12であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE13であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE14であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE15であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE16であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE17であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE18であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE19であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE20であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE21であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE22であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE23であるテトラゾリノン化合物。Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E11 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E12 . Tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E13 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E14 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E15 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E16 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E17 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E18 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E19 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E20 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E21 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E22 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E23 .
QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE24であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE25であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE26であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE27であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE28であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE29であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE30であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE31であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE32であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE33であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE34であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE35であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE36であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE37であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE38であるテトラゾリノン化合物。Tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E24 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E26 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E27 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E28 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; . A tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E30 . A tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E31 . A tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E32. . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E33 . Tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E34 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; . Tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E36 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E37 . Tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E38 .
QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE39であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE40であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE41であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE42であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE43であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE44であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE45であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE46であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE50であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE51であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE52であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE53であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE54であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE55であるテトラゾリノン化合物。A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E39. . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E40 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; and E is E41. . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E42 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E43 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E44 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E45. . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E46 . A tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E50 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E51 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E52 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E53 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E54 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E55 .
QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE56であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE57であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE58であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE59であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE60であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE61であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE62であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE63であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE64であるテトラゾリノン化合物。QがQ46であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE65であるテトラゾリノン化合物。A tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E56 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E57 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E58 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E59 . Tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E60 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E62 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; . Tetrazolinone compound wherein Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E64 . A tetrazolinone compound in which Q is Q46; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E65 .
QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE11であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE12であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE13であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE14であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE15であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE16であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE17であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE18であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE19であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE20であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE21であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE22であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE23であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE24であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE25であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE26であるテトラゾリノン化合物。Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; tetrazolinone compound E is E11. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; tetrazolinone compound E is E12. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; tetrazolinone compound E is E13. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; tetrazolinone compound E is E14. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is E15 tetrazolinone compound. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E16. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; tetrazolinone compound E is E17. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E18. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E19. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E20. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E21. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E22. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E23. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E24. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E25. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E26.
QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE27であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE28であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE29であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE30であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE31であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE32であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE33であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE34であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE35であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE36であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE37であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE38であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE39であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE40であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE41であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE42であるテトラゾリノン化合物。Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E27. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E28. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E29. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E30. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E31. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E32. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E33. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E34. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E35. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E36. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E37. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E38. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; tetrazolinone compound E is E39. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E40. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E41. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E42.
QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE43であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE44であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE45であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE46であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE50であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE51であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE52であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE53であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE54であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE55であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE56であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE57であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE58であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE59であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE60であるテトラゾリノン化合物。Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E43. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E44. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E45. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E46. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E50. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E51. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E52. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E53. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E54. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E55. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E56. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E57. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E58. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E59. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E60.
QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE61であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE62であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE63であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE64であるテトラゾリノン化合物。QがQ61であり;Yが−O−CH2−であり;R31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE65であるテトラゾリノン化合物。Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E61. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E62. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E63. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E64. Q There are at Q61; Y is -O-CH 2 - is; R 31 is hydrogen atom; R 5 is a methyl group; X is oxygen atom; E is tetrazolinone compound is E65.
Qが下記式Q400
〔式中、R30、R31、R32及びR33は前記と同じ意味を表し、$はAとの結合位置を表し、#はYとの結合位置を表す。〕であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE11であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE12であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE13であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE14であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE15であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE16であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE17であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE18であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE19であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R3がメチル基であり;Xが酸素原子であり;EがE20であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE21であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE22であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE23であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE24であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30およびR31が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE25であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE26であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE27であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE28であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE29であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE30であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE31であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE32であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE33であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE34であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE35であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE36であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE37であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE38であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE39であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE40であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE41であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE42であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE43であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE44であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE45であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE46であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE50であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE51であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE52であるテトラゾリノン化
合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE53であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE54であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE55であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE56であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE57であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE58であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE59であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE60であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE61であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE62であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE63であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE64であるテトラゾリノン化合物。QがQ400であり;Yが−O−CH2−であり;R30がメチル基であり;R31、R32およびR33が水素原子であり;R5がメチル基であり;Xが酸素原子であり;EがE65であるテトラゾリノン化合物。Q is the following formula Q400
[Wherein, R 30 , R 31 , R 32 and R 33 represent the same meaning as described above, $ represents a bonding position with A, and # represents a bonding position with Y. Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom Yes; a tetrazolinone compound in which E is E11. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E12. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E13. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E14. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E15. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E16. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E17. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E18. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E19. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 3 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E20. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E21. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E22. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E23. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E24; Tetrazolinone compound in which Q is Q400; Y is —O—CH 2 —; R 30 and R 31 are hydrogen atoms; R 5 is a methyl group; X is an oxygen atom; E is E25 . Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E26. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E27. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E28. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E29. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E30. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E31. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E32. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E33; Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E34; Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E35. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E36. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E37. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E38. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E39. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E40. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E41. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E42. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E43. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E44. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E45. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E46. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E50. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E51. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E52. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E53. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E54. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E55. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E56. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E57. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E58. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E59. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E60. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E61. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound in which E is E62; Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound which is an atom and E is E63. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E64. Q is Q400; Y is —O—CH 2 —; R 30 is a methyl group; R 31 , R 32 and R 33 are hydrogen atoms; R 5 is a methyl group; X is oxygen A tetrazolinone compound wherein E is E65.
EがE16であり、R8がC1−C6アルキル基であり、R3が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE16であり、R8がC1−C6アルキル基であり、R3が水素原子であり、QがQ46であり、R30およびR31が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE16であり、R8がC1−C6アルキル基であり、R3が水素原子であり、QがQ46であり、R30およびR31が水素原子であり、Yが−O−CH2−であり、Aが1以上のC1−C3アルコキシ基を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE16であり、R8がC1−C6アルキル基であり、R3が水素原子であり、QがQ61であり、R31が水素原子であり、Yが−O−CH2−であり、Aがアダマンチル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE16であり、R8がC1−C6アルキル基であり、R3が水素原子であり、QがQ61であり、R31が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。E is E16, R 8 is a C1-C6 alkyl group, R 3 is a hydrogen atom, Y is —O—CH 2 —, and A may have one or more halogen atoms. A tetrazolinone compound which is a phenyl group, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
E is E16, R 8 is a C1-C6 alkyl group, R 3 is a hydrogen atom, Q is Q46, R 30 and R 31 are hydrogen atoms, and Y is —O—CH 2 —. A tetrazolinone compound in which A is a phenyl group optionally having one or more halogen atoms, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
E is E16, R 8 is a C1-C6 alkyl group, R 3 is a hydrogen atom, Q is Q46, R 30 and R 31 are hydrogen atoms, and Y is —O—CH 2 —. A tetrazolinone compound in which A is a phenyl group optionally having one or more C1-C3 alkoxy groups, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
E is E16, R 8 is a C1-C6 alkyl group, R 3 is a hydrogen atom, Q is Q61, R 31 is a hydrogen atom, Y is —O—CH 2 —, A tetrazolinone compound in which A is an adamantyl group, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
E is E16, R 8 is a C1-C6 alkyl group, R 3 is a hydrogen atom, Q is Q61, R 31 is a hydrogen atom, Y is —O—CH 2 —, A tetrazolinone compound in which A is a phenyl group optionally having one or more halogen atoms, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
EがE19であり、R2およびR3が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE19であり、R2およびR3が水素原子であり、QがQ46であり、R30およびR31が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE19であり、R2およびR3が水素原子であり、QがQ61であり、R31が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。E is E19, R 2 and R 3 are hydrogen atoms, Y is —O—CH 2 —, A is a phenyl group optionally having one or more halogen atoms, and R 5 is A tetrazolinone compound which is a C1-C3 alkyl group and X is an oxygen atom.
E is E19, R 2 and R 3 are hydrogen atoms, Q is Q46, R 30 and R 31 are hydrogen atoms, Y is —O—CH 2 —, and A is 1 or more. A tetrazolinone compound which is a phenyl group optionally having a halogen atom, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
E is E19, R 2 and R 3 are hydrogen atoms, Q is Q61, R 31 is a hydrogen atom, Y is —O—CH 2 —, and A is one or more halogen atoms. A tetrazolinone compound which is a phenyl group which may have, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
EがE44であり、R6がC1−C6アルキル基であり、R3が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE44であり、R6がC1−C6アルキル基であり、R3が水素原子であり、QがQ46であり、R30およびR31が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。E is E44, R 6 is a C1-C6 alkyl group, R 3 is a hydrogen atom, Y is —O—CH 2 —, and A may have one or more halogen atoms. A tetrazolinone compound which is a phenyl group, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
E is E44, R 6 is a C1-C6 alkyl group, R 3 is a hydrogen atom, Q is Q46, R 30 and R 31 are hydrogen atoms, and Y is —O—CH 2 —. A tetrazolinone compound in which A is a phenyl group optionally having one or more halogen atoms, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
EがE51であり、R2、R3およびR4が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE51であり、R2、R3およびR4が水素原子であり、QがQ46であり、R30およびR31が水素原子であり、Yが−O−CH2−であり、Aが1以上のハロゲン原子を有していてもよいフェニル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。E is E51, R 2 , R 3 and R 4 are hydrogen atoms, Y is —O—CH 2 —, and A is a phenyl group optionally having one or more halogen atoms, A tetrazolinone compound in which R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
E is E51, R 2 , R 3 and R 4 are hydrogen atoms, Q is Q46, R 30 and R 31 are hydrogen atoms, Y is —O—CH 2 —, and A is A tetrazolinone compound which is a phenyl group optionally having one or more halogen atoms, R 5 is a C1-C3 alkyl group, and X is an oxygen atom.
EがE16であり、R8がC1−C6アルキル基であり、R3が水素原子であり、QがQ400であり、R30がC1−C3アルキル基であり、R31、R32およびR33が水素原子であり、Yが−O−CH2−であり、AがA17であり、R50が水素原子またはC1−C3アルキル基であり、R51がハロゲン原子であり、R59がC1−C3アルキル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。
EがE51であり、R2、R3およびR4が水素原子であり、QがQ400であり、R30がC1−C3アルキル基であり、R31、R32およびR33が水素原子であり、Yが−O−CH2−であり、AがA17であり、R50が水素原子またはC1−C3アルキル基であり、R51がハロゲン原子であり、R59がC1−C3アルキル基であり、R5がC1−C3アルキル基であり、Xが酸素原子であるテトラゾリノン化合物。E is E16, R 8 is a C1-C6 alkyl group, R 3 is a hydrogen atom, Q is Q400, R 30 is a C1-C3 alkyl group, R 31 , R 32 and R 33 Is a hydrogen atom, Y is —O—CH 2 —, A is A17, R 50 is a hydrogen atom or a C1-C3 alkyl group, R 51 is a halogen atom, and R 59 is C1- A tetrazolinone compound which is a C3 alkyl group, R 5 is a C1-C3 alkyl group, and X is an oxygen atom;
E is E51, R 2 , R 3 and R 4 are hydrogen atoms, Q is Q400, R 30 is a C1-C3 alkyl group, and R 31 , R 32 and R 33 are hydrogen atoms. Y is —O—CH 2 —, A is A17, R 50 is a hydrogen atom or a C1-C3 alkyl group, R 51 is a halogen atom, and R 59 is a C1-C3 alkyl group. , R 5 is a C1-C3 alkyl group, and X is an oxygen atom, a tetrazolinone compound.
次に、本発明化合物の製造法について説明する。
本発明化合物は、例えば以下の製造法により製造することができる。
(製造法A)
式(1)で示される本発明化合物(以下、化合物(1)と記す。)のうち、式(1A)で示される本発明化合物は、式(A1)で示される化合物(以下、化合物(A1)と記す。)と式(A2)で示される化合物(以下、化合物(A2)と記す。)とを塩基の存在下で反応させることにより製造することができる。
〔式中、R5、E、A、Q、X、およびGは前記と同じ意味を表し、Z11は塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基、トリフルオロメタンスルホニルオキシ基またはp−トルエンスルホニルオキシ基等の脱離基を表し、RA1およびRA2は、各々水素原子、ハロゲン原子またはC1−C3アルキル基を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、水およびこれらの混合物が挙げられる。
該反応に用いられる塩基としては、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム等のアルカリ金属水酸化物、フッ化ナトリウム、フッ化カリウム、フッ化セシウム等のアルカリ金属ハロゲン化物、水素化リチウム、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物、ナトリウムtert−ブトキシド、カリウムtert−ブトキシドのアルカリ金属アルコキシド等が挙げられる。
該反応には化合物(A1)1モルに対して、化合物(A2)が通常1〜10モルの割合、塩基が通常0.5〜5モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
該反応は、必要に応じてヨウ化ナトリウム、ヨウ化テトラブチルアンモニウムなどを加えてもよく、これらの化合物は通常、化合物(A1)1モルに対して、0.001〜1.2モルの割合で用いられる。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(1)を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。Next, the manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by the following production method.
(Production method A)
Of the compound of the present invention represented by formula (1) (hereinafter referred to as compound (1)), the compound of the present invention represented by formula (1A) is a compound represented by formula (A1) (hereinafter referred to as compound (A1)). And a compound represented by the formula (A2) (hereinafter referred to as compound (A2)) in the presence of a base.
[Wherein R 5 , E, A, Q, X, and G represent the same meaning as described above, and Z 11 represents a chlorine atom, a bromine atom, an iodine atom, a methanesulfonyloxy group, a trifluoromethanesulfonyloxy group, or p- A leaving group such as a toluenesulfonyloxy group is represented, and R A1 and R A2 each represent a hydrogen atom, a halogen atom, or a C1-C3 alkyl group. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene. Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc., lithium hydroxide, sodium hydroxide, Alkali metal hydroxides such as potassium hydroxide and cesium hydroxide, alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride, alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride , Nat Um tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
In the reaction, with respect to 1 mol of the compound (A1), the compound (A2) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 0.5 to 5 mol.
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
In the reaction, sodium iodide, tetrabutylammonium iodide or the like may be added as necessary, and these compounds are usually in a ratio of 0.001 to 1.2 mol with respect to 1 mol of the compound (A1). Used in
After completion of the reaction, the compound (1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
(製造法B)
化合物(1)は、式(B1)で示される化合物(以下、化合物(B1)と記す。)と式(B2)で示される化合物(以下、化合物(B2)と記す。)とを、塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、E、XおよびR5は前記と同じ意味を表し、Z21は塩素原子、臭素原子またはヨウ素原子を表し、Z31はB(OH)2、アルコキシボラニル基またはトリフルオロボレート塩(BF3 −K+)を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、メタノール、エタノール、プロパノール、ブタノール等のアルコール類、水およびこれらの混合物が挙げられる。
化合物(B2)は、通常市販のものを用いるか、N. Miyaura and A. Suzuki, Chem. Rev.,1995,95,2457等に記載された公知の方法により製造したものを用いることもできる。該反応に用いられる化合物(B2)は、例えば、Aのヨウ素化合物(A−I)、Aのブロモ化合物(A−Br)またはAのクロロ化合物(A−Cl)とブチルリチウムなどのアルキルリチウムとを反応させた後、ホウ酸エステルと反応させることによりボロン酸エステル誘導体を製造することができる。また、前述の反応で得られたボロン酸エステル誘導体を、必要に応じて加水分解することによりボロン酸誘導体を製造することができる。さらに、Molander et al.Acc.Chem.Res.,2007,40,275などに記載された公知の方法に従い、前記ボロン酸エステルをフッ化水素カリウム等でフッ素化することにより、トリフルオロボレート塩(BF3 −K+)を得ることもできる。
該反応に用いられる触媒としては、酢酸パラジウム(II)、ジクロロビス(トリフェニルホスフィン)パラジウム、テトラキストリフェニルホスフィンパラジウム(0)、パラジウム(II)アセテート/トリスシクロヘキシルホスフィン、ビス(ジフェニルホスファンフェロセニル)パラジウム(II)ジクロリド、1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾール−2−イリデン(1,4−ナフトキノン)パラジウムダイマー、アリル(クロロ)(1,3−ジメシチル−1,3−ジヒドロ−2H−イミダゾール−2−イリデン)パラジウムまたはパラジウム(II)アセテート/ジシクロヘキシル(2’,4’,6’−トリイソプロピルビフェニル−2−イル)ホスフィン、トリス(ジベンジリデンアセトン)ジパラジウム等が挙げられる。
該反応に用いられる塩基としては、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム等のアルカリ金属水酸化物、フッ化ナトリウム、フッ化カリウム、フッ化セシウム等のアルカリ金属ハロゲン化物、水素化リチウム、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物、リン酸三カリウム等のアルカリ金属リン酸塩、ナトリウムメトキシド、ナトリウムエトキシド、ナトリウムtert−ブトキシド、カリウムtert−ブトキシドのアルカリ金属アルコキシド等が挙げられる。
該反応には化合物(B1)1モルに対して、化合物(B2)が通常1〜10モルの割合、塩基が通常1〜10モルの割合、触媒が通常0.0001〜1モルの割合で用いられる。
該反応の反応温度は通常0〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(1)を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。(Production method B)
Compound (1) includes a compound represented by formula (B1) (hereinafter referred to as compound (B1)) and a compound represented by formula (B2) (hereinafter referred to as compound (B2)) as a base and It can be produced by subjecting it to a coupling reaction in the presence of a catalyst.
[Wherein, A, Q, Y, E, X and R 5 represent the same meaning as described above, Z 21 represents a chlorine atom, a bromine atom or an iodine atom, and Z 31 represents B (OH) 2 , alkoxyboranyl. Represents a group or a trifluoroborate salt (BF 3 − K + ). ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, methanol, ethanol, propanol, alcohols such as butanol, water and mixtures thereof.
As the compound (B2), a commercially available compound is generally used. Miyaura and A.M. Suzuki, Chem. Rev. , 1995, 95, 2457, etc., can also be used. The compound (B2) used in the reaction includes, for example, an iodine compound (AI) of A, a bromo compound (A-Br) of A, or a chloro compound (A-Cl) of A and an alkyllithium such as butyllithium. Then, the boronic acid ester derivative can be produced by reacting with boric acid ester. Moreover, a boronic acid derivative can be manufactured by hydrolyzing the boronic acid ester derivative obtained by the above-mentioned reaction as needed. In addition, Molander et al. Acc. Chem. Res. , 2007, 40, 275 and the like, by fluorinating the boronic acid ester with potassium hydrogen fluoride or the like, a trifluoroborate salt (BF 3 − K + ) can also be obtained.
Catalysts used in the reaction include palladium (II) acetate, dichlorobis (triphenylphosphine) palladium, tetrakistriphenylphosphinepalladium (0), palladium (II) acetate / triscyclohexylphosphine, bis (diphenylphosphaneferrocenyl) ) Palladium (II) dichloride, 1,3-bis (2,6-diisopropylphenyl) imidazol-2-ylidene (1,4-naphthoquinone) palladium dimer, allyl (chloro) (1,3-dimesityl-1,3- Dihydro-2H-imidazol-2-ylidene) palladium or palladium (II) acetate / dicyclohexyl (2 ′, 4 ′, 6′-triisopropylbiphenyl-2-yl) phosphine, tris (dibenzylideneacetone) dipalladium And the like.
Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene. Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc., lithium hydroxide, sodium hydroxide, Alkali metal hydroxides such as potassium hydroxide and cesium hydroxide, alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride, alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride ,Rin Alkali metal phosphates such as tripotassium, sodium methoxide, sodium ethoxide, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
In this reaction, 1 mol of compound (B2) is usually used in a proportion of 1 to 10 mol, a proportion of base is usually 1 to 10 mol, and a catalyst is usually used in a proportion of 0.0001 to 1 mol with respect to 1 mol of compound (B1) It is done.
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
(製造法C)
化合物(1)は、式(C1)で示される化合物(以下、化合物(C1)と記す。)と式(C2)で示される化合物(以下、化合物(C2)と記す。)とを、塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、E、X、R5、Z21およびZ31は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、水およびこれらの混合物が挙げられる。
化合物(C2)は、通常、公知の方法で製造したもの、もしくは、市販のものを用いることができる。
該反応に用いられる触媒としては、酢酸パラジウム(II)、ジクロロビス(トリフェニルホスフィン)パラジウム、テトラキストリフェニルホスフィンパラジウム(0)、パラジウム(II)アセテート/トリスシクロヘキシルホスフィン、ビス(ジフェニルホスファンフェロセニル)パラジウム(II)ジクロリド、1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾール−2−イリデン(1,4−ナフトキノン)パラジウムダイマー、アリル(クロロ)(1,3−ジメシチル−1,3−ジヒドロ−2H−イミダゾール−2−イリデン)パラジウムまたはパラジウム(II)アセテート/ジシクロヘキシル(2’,4’,6’−トリイソプロピルビフェニル−2−イル)ホスフィン、トリス(ジベンジリデンアセトン)ジパラジウム等が挙げられる。
該反応に用いられる塩基としては、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム等のアルカリ金属水酸化物、フッ化ナトリウム、フッ化カリウム、フッ化セシウム等のアルカリ金属ハロゲン化物、水素化リチウム、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物、リン酸三カリウム等のアルカリ金属リン酸塩、ナトリウムメトキシド、ナトリウムエトキシド、ナトリウムtert−ブトキシド、カリウムtert−ブトキシドのアルカリ金属アルコキシド等が挙げられる。
該反応には化合物(C1)1モルに対して、化合物(C2)が通常1〜10モルの割合、塩基が通常1〜10モルの割合、触媒が通常0.0001〜1モルの割合で用いられる。
該反応の反応温度は通常0〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(1)を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。(Production method C)
Compound (1) includes a compound represented by formula (C1) (hereinafter referred to as compound (C1)) and a compound represented by formula (C2) (hereinafter referred to as compound (C2)), a base and It can be produced by subjecting it to a coupling reaction in the presence of a catalyst.
[Wherein, A, Q, Y, E, X, R 5 , Z 21 and Z 31 represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
As compound (C2), a compound produced by a known method or a commercially available compound can be used.
Catalysts used in the reaction include palladium (II) acetate, dichlorobis (triphenylphosphine) palladium, tetrakistriphenylphosphinepalladium (0), palladium (II) acetate / triscyclohexylphosphine, bis (diphenylphosphaneferrocenyl) ) Palladium (II) dichloride, 1,3-bis (2,6-diisopropylphenyl) imidazol-2-ylidene (1,4-naphthoquinone) palladium dimer, allyl (chloro) (1,3-dimesityl-1,3- Dihydro-2H-imidazol-2-ylidene) palladium or palladium (II) acetate / dicyclohexyl (2 ′, 4 ′, 6′-triisopropylbiphenyl-2-yl) phosphine, tris (dibenzylideneacetone) dipalladium And the like.
Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene. Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc., lithium hydroxide, sodium hydroxide, Alkali metal hydroxides such as potassium hydroxide and cesium hydroxide, alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride, alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride ,Rin Alkali metal phosphates such as tripotassium, sodium methoxide, sodium ethoxide, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
In this reaction, 1 mol of the compound (C2) is usually used in a proportion of 1 to 10 mol, 1 to 10 mol of the base, and 0.0001 to 1 mol of the catalyst is usually used in the reaction with respect to 1 mol of the compound (C1). It is done.
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
(製造法D)
化合物(1)は、式(1−3)で示される化合物(以下、化合物(1−3)と記す。)と式(E1)で示される化合物(以下、化合物(E1)と記す。)とを塩基の存在下で反応させることにより製造することができる。
〔式中、A、Q、Y、E、X、R5およびZ11は前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、水およびこれらの混合物が挙げられる。
該反応に用いられる化合物(E1)は、通常市販のものを用いることができる。具体的には、クロロジフルオロメタン、臭化メチル、臭化エチル、臭化プロピル、ヨウ化メチル、ヨウ化エチル、ヨウ化プロピル、1,1−ジフルオロ−2−ヨードエタン等のハロゲン化アルキル類、硫酸ジメチル等の硫酸ジアルキル類、p−トルエンスルホン酸メチル、p−トルエンスルホン酸エチル、p−トルエンスルホン酸プロピル、メタンスルホン酸メチル、メタンスルホン酸エチル、メタンスルホン酸プロピル等のアルキルおよびアリールスルホン酸エステル類等が挙げられる。
該反応に用いられる塩基としては、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム等のアルカリ金属水酸化物、フッ化ナトリウム、フッ化カリウム、フッ化セシウム等のアルカリ金属ハロゲン化物、水素化リチウム、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物、水素化リチウム、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物、ナトリウムtert−ブトキシド、カリウムtert−ブトキシドのアルカリ金属アルコキシド等が挙げられる。
該反応には化合物(1−3)1モルに対して、化合物(E1)が通常1〜10モルの割合、塩基が通常1〜10モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(1)を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。(Production Method D)
Compound (1) includes a compound represented by formula (1-3) (hereinafter referred to as compound (1-3)) and a compound represented by formula (E1) (hereinafter referred to as compound (E1)). Can be prepared by reacting in the presence of a base.
[Wherein, A, Q, Y, E, X, R 5 and Z 11 represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
As the compound (E1) used for the reaction, a commercially available product can be used. Specifically, alkyl halides such as chlorodifluoromethane, methyl bromide, ethyl bromide, propyl bromide, methyl iodide, ethyl iodide, propyl iodide, 1,1-difluoro-2-iodoethane, sulfuric acid Dialkyl sulfates such as dimethyl, alkyl p-toluenesulfonate, ethyl p-toluenesulfonate, propyl p-toluenesulfonate, methyl methanesulfonate, ethyl methanesulfonate, propyl methanesulfonate, and arylsulfonates And the like.
Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene. Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc., lithium hydroxide, sodium hydroxide, Alkali metal hydroxides such as potassium hydroxide and cesium hydroxide, alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride, alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride ,hydrogen Lithium, sodium hydride, an alkali metal hydride such as potassium hydride, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
In the reaction, with respect to 1 mol of the compound (1-3), the compound (E1) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
(製造法E)
化合物(1)のうちXが硫黄原子である化合物(以下、化合物(1−S)と記す。)は、化合物(1)のうちXが酸素原子である化合物(以下、化合物(1−O)と記す。)と硫化剤とを反応させることにより製造することができる。
〔式中、A、Q、Y、EおよびR5は前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類およびこれらの混合物が挙げられる。
該反応に用いられる硫化剤としては五硫化リン、ローソン試薬(2,4−Bis(4−methoxyphenyl)−1,3,2,4−dithiadiphosphetane 2,4−disulfide)が挙げられる。
該反応には、硫化剤が、化合物(1−O)1モルに対して好ましくは0.5〜1.5モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
該反応は、必要に応じてピリジンやトリエチルアミンなどの有機塩基、アルカリ金属水酸化物やアルカリ金属炭酸塩などの無機塩基などを加えてもよく、添加する塩基の使用量は化合物(1−O)に対して0.5〜1.5モルである。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(1−S)を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。(Production method E)
Of the compound (1), a compound in which X is a sulfur atom (hereinafter referred to as compound (1-S)) is a compound in which X is an oxygen atom in compound (1) (hereinafter referred to as compound (1-O)). It can be produced by reacting a sulfurizing agent.
[Wherein, A, Q, Y, E and R 5 represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as tellurium, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, nitriles such as acetonitrile, propionitrile, etc. And mixtures thereof.
Examples of the sulfurizing agent used in the reaction include phosphorus pentasulfide and Lawesson's reagent (2,4-bis (4-methoxyphenyl) -1,3,2,4-dithiadiphosphatane 2,4-disulphide).
In the reaction, a sulfiding agent is preferably used at a ratio of 0.5 to 1.5 mol with respect to 1 mol of the compound (1-O).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
In the reaction, if necessary, an organic base such as pyridine or triethylamine, an inorganic base such as an alkali metal hydroxide or an alkali metal carbonate, or the like may be added. The amount of the base to be added is the compound (1-O). It is 0.5-1.5 mol with respect to.
After completion of the reaction, the compound (1-S) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
(製造法F)
化合物(1)のうち、式(1−4)で示される化合物(以下、化合物(1−4)と記す。)は、式(G1)で示される化合物(以下、化合物(G1)と記す。)と式(G21)で示される化合物(以下、化合物(G21)と記す。)とを、塩基及び触媒存在下カップリング反応することにより製造することができる。
〔式中、A、Q、Y、X、R5、Z2、Z3、Z4およびZ31は前記と同じ意味を表し、Z41は塩素原子、臭素原子、ヨウ素原子またはトリフルオロメタンスルホニルオキシ基を表し、R71は
C1−C6アルキル基、C1−C6ハロアルキル基、C2−C6アルケニル基、C2−C6ハロアルケニル基、C2−C6アルキニル基、C2−C6ハロアルキニル基、C3−Cシクロアルキル基、またはC3−C6ハロシクロアルキル基を表す。ただし、Z2、Z3およびZ4のうち、少なくとも1つは窒素原子を表す。〕
該反応は、製造法Bに準じて実施することができる。(Production Method F)
Among compounds (1), a compound represented by formula (1-4) (hereinafter referred to as compound (1-4)) is represented by a compound represented by formula (G1) (hereinafter referred to as compound (G1)). ) And a compound represented by formula (G21) (hereinafter referred to as compound (G21)) can be produced by a coupling reaction in the presence of a base and a catalyst.
[Wherein, A, Q, Y, X, R 5 , Z 2 , Z 3 , Z 4 and Z 31 represent the same meaning as described above, and Z 41 represents a chlorine atom, a bromine atom, an iodine atom or trifluoromethanesulfonyloxy. R 71 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C2-C6 haloalkenyl group, a C2-C6 alkynyl group, a C2-C6 haloalkynyl group, a C3-C cycloalkyl group. Group or a C3-C6 halocycloalkyl group. However, at least one of Z 2 , Z 3 and Z 4 represents a nitrogen atom. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−5)で示される化合物(以下、化合物(1−5)と記す。)は、式(G2)で示される化合物(以下、化合物(G2)と記す。)と式(G22)で示される化合物(以下、化合物(G22)と記す。)とを塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、X、R5、Z1、Z3、Z4、Z31およびZ41は前記と同じ意味を表し、R72はC1−C3アルキル基を表す。ただし、Z1、Z3およびZ4のうち、少なくとも1つは窒素原子を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (1-5) (hereinafter referred to as compound (1-5)) is represented by a compound represented by formula (G2) (hereinafter referred to as compound (G2)). ) And a compound represented by the formula (G22) (hereinafter referred to as compound (G22)) are subjected to a coupling reaction in the presence of a base and a catalyst.
[Wherein, A, Q, Y, X, R 5 , Z 1 , Z 3 , Z 4 , Z 31 and Z 41 represent the same meaning as described above, and R 72 represents a C1-C3 alkyl group. However, at least one of Z 1 , Z 3 and Z 4 represents a nitrogen atom. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−6)で示される化合物(以下、化合物(1−6)と記す。)は、式(G3)で示される化合物(以下、化合物(G3)と記す。)と化合物(G22)とを塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、X、R5、R72、Z1、Z2、Z4、Z31およびZ41は前記と同じ意味を表す。ただし、Z1、Z2およびZ4のうち、少なくとも1つは窒素原子を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (1-6) (hereinafter referred to as compound (1-6)) is represented by a compound represented by formula (G3) (hereinafter referred to as compound (G3)). ) And compound (G22) can be produced by subjecting them to a coupling reaction in the presence of a base and a catalyst.
[Wherein, A, Q, Y, X, R 5 , R 72 , Z 1 , Z 2 , Z 4 , Z 31 and Z 41 represent the same meaning as described above. However, at least one of Z 1 , Z 2 and Z 4 represents a nitrogen atom. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−7)で示される化合物(以下、化合物(1−7)と記す。)は、式(G4)で示される化合物(以下、化合物(G4)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、X、R5、R72、Z1、Z2、Z3、Z31およびZ41は前記と同じ意味を表す。ただし、Z1、Z2およびZ3のうち、少なくとも1つは窒素原子を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (1-7) (hereinafter referred to as compound (1-7)) is represented by a compound represented by formula (G4) (hereinafter referred to as compound (G4)). And the compound (G22) in the presence of a base and a catalyst in a coupling reaction.
[Wherein, A, Q, Y, X, R 5 , R 72 , Z 1 , Z 2 , Z 3 , Z 31 and Z 41 represent the same meaning as described above. However, at least one of Z 1 , Z 2 and Z 3 represents a nitrogen atom. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−8)で示される化合物(以下、化合物(1−8)と記す。)は、式(G5)で示される化合物(以下、化合物(G5)と記す。)とを化合物(G21)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、Y2、X、R5、R71、Z3、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (1-8) (hereinafter referred to as compound (1-8)) is represented by a compound represented by formula (G5) (hereinafter referred to as compound (G5)). Can be produced by subjecting compound (G21) to a coupling reaction in the presence of a base and a catalyst.
[Wherein, A, Q, Y, Y 2 , X, R 5 , R 71 , Z 3 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−9)で示される化合物(以下、化合物(1−9)と記す。)は、式(G6)で示される化合物(以下、化合物(G6)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、Y2、X、R5、R72、Z1、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (1-9) (hereinafter referred to as compound (1-9)) is represented by a compound represented by formula (G6) (hereinafter referred to as compound (G6)). And the compound (G22) in the presence of a base and a catalyst in a coupling reaction.
[Wherein, A, Q, Y, Y 2 , X, R 5 , R 72 , Z 1 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−10)で示される化合物(以下、化合物(1−10)と記す。)は、式(G7)で示される化合物(以下、化合物(G7)と記す。)とを化合物(G21)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、Y3、X、R5、R71、Z2、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (1-10) (hereinafter referred to as compound (1-10)) is represented by a compound represented by formula (G7) (hereinafter referred to as compound (G7)). Can be produced by subjecting compound (G21) to a coupling reaction in the presence of a base and a catalyst.
[Wherein, A, Q, Y, Y 3 , X, R 5 , R 71 , Z 2 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−11)で示される化合物(以下、化合物(1−11)と記す。)は、式(G8)で示される化合物(以下、化合物(G8)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、Y3、X、R5、R72、Z1、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (1-11) (hereinafter referred to as compound (1-11)) is represented by a compound represented by formula (G8) (hereinafter referred to as compound (G8)). And the compound (G22) in the presence of a base and a catalyst in a coupling reaction.
[Wherein, A, Q, Y, Y 3 , X, R 5 , R 72 , Z 1 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−12)で示される化合物(以下、化合物(1−12)と記す。)は、式(G9)で示される化合物(以下、化合物(G9)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、Y1、X、R5、R72、Z3、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (1-12) (hereinafter referred to as compound (1-12)) is represented by a compound represented by formula (G9) (hereinafter referred to as compound (G9)). And the compound (G22) in the presence of a base and a catalyst in a coupling reaction.
[Wherein, A, Q, Y, Y 1 , X, R 5 , R 72 , Z 3 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(1−13)で示される化合物(以下、化合物(1−13)と記す。)は、式(G10)で示される化合物(以下、化合物(G10)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Q、Y、Y1、X、R5、R72、Z2、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。
製造法Bのカップリング反応に代えて、他の公知のカップリング反応を用いることにより、化合物(1)を製造することもできる。Among compounds (1), a compound represented by formula (1-13) (hereinafter referred to as compound (1-13)) is represented by a compound represented by formula (G10) (hereinafter referred to as compound (G10)). And the compound (G22) in the presence of a base and a catalyst in a coupling reaction.
[Wherein, A, Q, Y, Y 1 , X, R 5 , R 72 , Z 2 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
In place of the coupling reaction of Production Method B, compound (1) can also be produced by using another known coupling reaction.
(製造法G)
化合物(1)のうちQがQ46である式(1−H)で示される化合物(以下、化合物(1−H)と記す。)は、式(H1)で示される化合物(以下、化合物(H1)と記す。)と式(H2)で示される化合物(以下、化合物(H2)と記す。)とを、塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、A、Y、E、R5、X、R30、R31およびZ31は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、水およびこれらの混合物が挙げられる。
該反応に用いられる化合物(H2)は、通常市販のものを用いることができる。
該反応に用いられる触媒としては、酢酸銅、ヨウ化銅、臭化銅、塩化銅、酢酸パラジウム(II)、ジクロロビス(トリフェニルホスフィン)パラジウム、テトラキストリフェニルホスフィンパラジウム(0)、パラジウム(II)アセテート/トリスシクロヘキシルホスフィン、ビス(ジフェニルホスファンフェロセニル)パラジウム(II)ジクロリド、1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾール−2−イリデン(1,4−ナフトキノン)パラジウムダイマー、アリル(クロロ)(1,3−ジメシチル−1,3−ジヒドロ−2H−イミダゾール−2−イリデン)パラジウムまたはパラジウム(II)アセテート/ジシクロヘキシル(2’,4’,6’−トリイソプロピルビフェニル−2−イル)ホスフィン、トリス(ジベンジリデンアセトン)ジパラジウム等が挙げられる。
該反応に用いられる塩基としては、ピリジン、トリエチルアミン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム等のアルカリ金属水酸化物、フッ化ナトリウム、フッ化カリウム、フッ化セシウム等のアルカリ金属ハロゲン化物、水素化リチウム、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物、リン酸三カリウム等のアルカリ金属リン酸塩、ナトリウムメトキシド、ナトリウムエトキシド、ナトリウムtert−ブトキシド、カリウムtert−ブトキシドのアルカリ金属アルコキシド等が挙げられる。
該反応には化合物(H1)1モルに対して、化合物(H2)が通常1〜10モルの割合、塩基が通常1〜10モルの割合、触媒が通常0.0001〜1モルの割合で用いられる。
該反応の反応温度は通常0〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(1−H)を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。(Production method G)
Among compounds (1), a compound represented by formula (1-H) in which Q is Q46 (hereinafter referred to as compound (1-H)) is a compound represented by formula (H1) (hereinafter referred to as compound (H1). ) And a compound represented by formula (H2) (hereinafter referred to as compound (H2)) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein, A, Y, E, R 5 , X, R 30 , R 31 and Z 31 represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
As the compound (H2) used in the reaction, a commercially available compound can be used.
The catalyst used in the reaction includes copper acetate, copper iodide, copper bromide, copper chloride, palladium acetate (II), dichlorobis (triphenylphosphine) palladium, tetrakistriphenylphosphine palladium (0), palladium (II). Acetate / triscyclohexylphosphine, bis (diphenylphosphaneferrocenyl) palladium (II) dichloride, 1,3-bis (2,6-diisopropylphenyl) imidazol-2-ylidene (1,4-naphthoquinone) palladium dimer, allyl (Chloro) (1,3-dimesityl-1,3-dihydro-2H-imidazol-2-ylidene) palladium or palladium (II) acetate / dicyclohexyl (2 ′, 4 ′, 6′-triisopropylbiphenyl-2-yl) ) Phosphine, tris (di Nji) dipalladium and the like.
Examples of the base used in the reaction include organic bases such as pyridine, triethylamine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene. Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc., lithium hydroxide, sodium hydroxide, Alkali metal hydroxides such as potassium hydroxide and cesium hydroxide, alkali metal halides such as sodium fluoride, potassium fluoride and cesium fluoride, alkali metal hydrides such as lithium hydride, sodium hydride and potassium hydride ,Rin Alkali metal phosphates such as tripotassium, sodium methoxide, sodium ethoxide, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
In this reaction, 1 mol of compound (H2) is usually used in a proportion of 1 to 10 mol, a proportion of base is usually 1 to 10 mol, and a catalyst is usually used in a proportion of 0.0001 to 1 mol with respect to 1 mol of compound (H1). It is done.
The reaction temperature is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (1-H) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
以下に中間体化合物の合成方法について詳細に記載する。
(参考製造法A)
式(XA3)で示される化合物(以下、化合物(XA3)と記す。)は、式(XA1)で示される化合物(以下、化合物(XA1)と記す。)または(XA2)で示される化合物(以下、化合物(XA2)と記す。)とアジド化剤とを反応させることにより製造することができる。
〔式中、RA1、RA2、Y、E、A、QおよびXは前記と同じ意味を表し、R101はP11、P12またはP13を表し、R91はC1−C12アルキル基を表し、Z101は塩素原子または臭素原子を表し、波線は結合部位を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類およびこれらの混合物が挙げられる。
該反応に用いられるアジド化剤としては例えばアジ化ナトリウム、アジ化バリウムまたはアジ化リチウム等の無機アジド類、アジ化トリメチルシリル、アジ化ジフェニルホスホリル等の有機アジド類が挙げられる。
該反応には化合物(XA1)または化合物(XA2)1モルに対して、アジド化剤が通常1〜10モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
該反応は、必要に応じて、塩化アルミニウムもしくは塩化亜鉛等のルイス酸を加えてもよく、これらの化合物は通常、化合物(XA1)または化合物(XA2)1モルに対して、0.05〜5モルの割合で用いられる。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XA3)を単離することができる。単離された化合物(XA3)は、クロマトグラフィー、再結晶等によりさらに精製することもできる。The method for synthesizing the intermediate compound is described in detail below.
(Reference production method A)
A compound represented by formula (XA3) (hereinafter referred to as compound (XA3)) is a compound represented by formula (XA1) (hereinafter referred to as compound (XA1)) or a compound represented by (XA2) (hereinafter referred to as “XA2”). , Described as Compound (XA2)) and an azidating agent.
[Wherein, R A1 , R A2 , Y, E, A, Q and X represent the same meaning as described above, R 101 represents P 11 , P 12 or P 13 , and R 91 represents a C1-C12 alkyl group. Z 101 represents a chlorine atom or a bromine atom, and a wavy line represents a binding site. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, acetonitrile, nitriles and mixtures thereof, such as propionitrile and the like.
Examples of the azidating agent used in the reaction include inorganic azides such as sodium azide, barium azide or lithium azide, and organic azides such as trimethylsilyl azide and diphenylphosphoryl azide.
In the reaction, the azidating agent is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (XA1) or the compound (XA2).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
In this reaction, a Lewis acid such as aluminum chloride or zinc chloride may be added as necessary, and these compounds are usually added in an amount of 0.05 to 5 to 1 mol of compound (XA1) or compound (XA2). Used in molar proportions.
After completion of the reaction, the compound (XA3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound (XA3) can be further purified by chromatography, recrystallization, and the like.
(参考製造法B)
化合物(XA1)は、式(XB1)で示される化合物(以下、化合物(XB1)と記す。)とイソシアナート化剤とを反応させることにより製造することができる。
〔式中、R101、EおよびXは前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸メチル等のエステル類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類およびこれらの混合物が挙げられる。
該反応に用いられるイソシアナート化剤としては、例えば、ホスゲン、ジホスゲン、トリホスゲン、チオホスゲン、N,N−カルボジイミダゾールおよびN,N−チオカルボジイミダゾール等が挙げられる。
該反応には化合物(XB1)1モルに対して、イソシアナート化剤が通常0.34〜10モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
該反応は、必要に応じて、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩等を加えてもよく、これらの化合物は通常、化合物(XB1)1モルに対して、0.05〜5モルの割合で用いられる。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XA1)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method B)
Compound (XA1) can be produced by reacting a compound represented by formula (XB1) (hereinafter referred to as compound (XB1)) with an isocyanate agent.
[Wherein R 101 , E and X represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether and diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene, esters such as ethyl acetate and methyl acetate , Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, and mixtures thereof.
Examples of the isocyanate agent used in the reaction include phosgene, diphosgene, triphosgene, thiophosgene, N, N-carbodiimidazole, N, N-thiocarbodiimidazole, and the like.
In this reaction, an isocyanate agent is usually used in a proportion of 0.34 to 10 mol per 1 mol of compound (XB1).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
The reaction may be carried out by using organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene, etc. , Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc. The compound is usually used at a ratio of 0.05 to 5 mol with respect to 1 mol of compound (XB1).
After completion of the reaction, the compound (XA1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法C)
化合物(XA2)は、式(XC1)で示される化合物(以下、化合物(XC1)と記す。)とハロゲン化剤とを反応させることにより製造することができる。
〔式中、R101、EおよびZ101は前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸メチル等のエステル類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類およびこれらの混合物が挙げられる。
該反応に用いられるハロゲン化剤としては、例えば、オキシ塩化リン、三塩化リン、五塩化リン、塩化チオニル、オキシ臭化リン、三臭化リン、五臭化リン、三ヨウ化リン、二塩化オキサリル、二臭化オキサリル、トリホスゲン、ジホスゲン、ホスゲンおよび塩化スルフリル等が挙げられる。
該反応には化合物(XC1)1モルに対して、ハロゲン化剤が通常1〜10モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
該反応は触媒を加えてもよく、ジメチルホルムアミド等が用いられる。触媒の使用量は、通常、化合物(XC1)1モルに対して、0.001〜1モルの割合で用いられる。
該反応は、必要に応じて、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩等を加えてもよく、これらの化合物は通常、化合物(XC1)1モルに対して、0.05〜5モルの割合で用いられる。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XA2)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method C)
Compound (XA2) can be produced by reacting a compound represented by the formula (XC1) (hereinafter referred to as compound (XC1)) with a halogenating agent.
[Wherein R 101 , E and Z 101 represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether and diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene, esters such as ethyl acetate and methyl acetate , Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, and mixtures thereof.
Examples of the halogenating agent used in the reaction include phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl chloride, phosphorus oxybromide, phosphorus tribromide, phosphorus pentabromide, phosphorus triiodide, and dichloride. Examples include oxalyl, oxalyl dibromide, triphosgene, diphosgene, phosgene, and sulfuryl chloride.
In the reaction, the halogenating agent is generally used in a proportion of 1 to 10 mol per 1 mol of the compound (XC1).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
In the reaction, a catalyst may be added, and dimethylformamide or the like is used. The amount of the catalyst to be used is generally 0.001 to 1 mol per 1 mol of compound (XC1).
The reaction may be carried out with an organic base such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene as necessary. , Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc. The compound is usually used at a ratio of 0.05 to 5 mol with respect to 1 mol of compound (XC1).
After completion of the reaction, the compound (XA2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法D)
化合物(XA1)は、化合物(XB1)とカーバメート化剤とを反応させ、式(XD1)で示される化合物(以下、化合物(XD1)と記す。)を得たのち、化合物(XD1)とイソシアナート化剤とを反応させることにより製造することができる。
〔式中、R101、EおよびXは前記と同じ意味を表し、R111はC1−C12アルキル基またはフェニル基を表す。〕(Reference production method D)
Compound (XA1) is obtained by reacting compound (XB1) with a carbamate agent to obtain a compound represented by formula (XD1) (hereinafter referred to as compound (XD1)), and then compound (XD1) and isocyanate. It can be produced by reacting with an agent.
[Wherein, R 101 , E and X represent the same meaning as described above, and R 111 represents a C1-C12 alkyl group or a phenyl group. ]
以下に化合物(XB1)から化合物(XD1)を製造する方法を説明する。
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、水およびこれらの混合物が挙げられる。
該反応に用いられるカーバメート化剤としては、クロロ炭酸フェニル、クロロ炭酸メチル、クロロ炭酸エチル、クロロ炭酸n−プロピル、クロロ炭酸イソプロピル、クロロ炭酸n−ブチル、クロロ炭酸tert−ブチル、二炭酸ジ−tert−ブチル、二炭酸ジメチル、二炭酸ジエチル、クロロチオぎ酸O−フェニル、クロロチオぎ酸O−メチル、クロロチオぎ酸O−エチル等が挙げられる。
該反応には化合物(XB1)1モルに対して、カーバメート化剤が通常1〜10モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
該反応は、必要に応じて、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩等を加えてもよく、これらの化合物は通常、化合物(XB1)1モルに対して、0.05〜5モルの割合で用いられる。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XD1)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。A method for producing compound (XD1) from compound (XB1) will be described below.
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
Carbamate agents used in the reaction include phenyl chlorocarbonate, methyl chlorocarbonate, ethyl chlorocarbonate, n-propyl chlorocarbonate, isopropyl chlorocarbonate, n-butyl chlorocarbonate, tert-butyl chlorocarbonate, di-tert dicarbonate. -Butyl, dimethyl dicarbonate, diethyl dicarbonate, O-phenyl chlorothioformate, O-methyl chlorothioformate, O-ethyl chlorothioformate and the like.
In the reaction, the carbamate is usually used at a ratio of 1 to 10 moles with respect to 1 mole of the compound (XB1).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
The reaction may be carried out by using organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene, etc. , Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc. The compound is usually used at a ratio of 0.05 to 5 mol with respect to 1 mol of compound (XB1).
After completion of the reaction, the compound (XD1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
以下に化合物(XD1)から化合物(XA1)を製造する方法を説明する。
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、テトラヒドロフラン、ジオキサン、エチレングリコ−ルジメチルエ−テル、メチルtert−ブチルエーテル等のエ−テル類、トルエン、キシレン等の芳香族炭化水素類、四塩化炭素、クロロホルムまたは1,2−ジクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、アセトニトリル等のニトリル類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類及びこれらの混合物が挙げられる。
該反応に用いられるイソシアナート化剤としては、例えば、五塩化リン、オキシ塩化リン、五酸化二リン、トリクロロシラン、ジクロロシラン、モノクロロシラン、三塩化ホウ素、2−クロロ−1,3,2−ベンゾジオキサボロール、二ヨウ化シラン、メチルトリクロロシラン、ジメチルジクロロシラン、クロロトリメチルシラン等を用いることができる。
該反応には化合物(XD1)1モルに対して、イソシアナート化剤が通常1〜10モルの割合で用いられる。
該反応の反応温度は通常−20〜250℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
該反応は、必要に応じて、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩等を加えてもよく、これらの化合物は通常、化合物(XD1)1モルに対して、0.05〜5モルの割合で用いられる。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XA1)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。A method for producing compound (XA1) from compound (XD1) will be described below.
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran, dioxane, ethylene glycol dimethyl ether and methyl tert-butyl ether, aromatic hydrocarbons such as toluene and xylene, carbon tetrachloride, chloroform or Halogenated hydrocarbons such as 1,2-dichloroethane and chlorobenzene, nitriles such as acetonitrile, acid amides such as N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone, Examples thereof include sulfoxides such as dimethyl sulfoxide, ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone, and mixtures thereof.
Examples of the isocyanate agent used in the reaction include phosphorus pentachloride, phosphorus oxychloride, diphosphorus pentoxide, trichlorosilane, dichlorosilane, monochlorosilane, boron trichloride, 2-chloro-1,3,2- Benzodioxaborol, diiodinated silane, methyltrichlorosilane, dimethyldichlorosilane, chlorotrimethylsilane, and the like can be used.
In the reaction, the isocyanate agent is usually used in a proportion of 1 to 10 mol per 1 mol of the compound (XD1).
The reaction temperature is usually in the range of -20 to 250 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
The reaction may be carried out with an organic base such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene as necessary. , Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc. The compound is usually used at a ratio of 0.05 to 5 mol per 1 mol of compound (XD1).
After completion of the reaction, the compound (XA1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法E)
式(XB1)で示される化合物は、式(XE1)で示される化合物(以下、化合物(XE1)と記す。)を、過剰量の水素雰囲気中で、触媒と反応させることにより製造することができる。
〔式中、R101およびEは前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、メタノール、エタノール、プロパノール、ブタノール等のアルコール類、酢酸エチル、酢酸ブチル等のエステル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエ−テル類、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、水およびこれらの混合物が挙げられる。
該反応に用いられる触媒として、パラジウム担持炭素(Pd/C)、白金担持炭素(Pt/C)、オスミウム担持炭素(Os/C)、ルテニウム担持炭素(Ru/C)、ロジウム担持炭素(Rh/C)、ラネーニッケル等をあげることができる。
該反応には化合物(XE1)1モルに対して、触媒が通常0.0001〜1モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、触媒を濾過後、有機層を濃縮する等の後処理操作を行うことにより、化合物(XB1)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method E)
The compound represented by the formula (XB1) can be produced by reacting the compound represented by the formula (XE1) (hereinafter referred to as the compound (XE1)) with a catalyst in an excessive amount of hydrogen atmosphere. .
[Wherein R 101 and E represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include alcohols such as methanol, ethanol, propanol and butanol, esters such as ethyl acetate and butyl acetate, carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, Halogenated hydrocarbons such as chlorobenzene, ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisole, methyl tert-butyl ether, diisopropyl ether, n-heptane, n-hexane , Hydrocarbons such as cyclohexane, n-pentane, toluene, xylene, water, and mixtures thereof.
Catalysts used in the reaction include palladium on carbon (Pd / C), platinum on carbon (Pt / C), osmium on carbon (Os / C), ruthenium on carbon (Ru / C), rhodium on carbon (Rh / C), Raney nickel and the like.
In the reaction, the catalyst is usually used in a proportion of 0.0001 to 1 mol with respect to 1 mol of the compound (XE1).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XB1) can be isolated by performing post-treatment operations such as filtration of the catalyst and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法F)
化合物(XB1)は、酸の存在下で化合物(XE1)と還元剤とを反応することにより製造することができる。
〔式中、R101およびEは前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、溶媒としては、酢酸等の脂肪族カルボン酸類、メタノール、エタノール等のアルコール類、水およびそれらの混合物が挙げられる。
該反応に用いられる還元剤としては、例えば、鉄、スズ、および亜鉛が挙げられる。
該反応に用いられる酸としては、例えば、塩酸、硫酸、酢酸、および塩化アンモニウム水溶液が挙げられる。
該反応には化合物(XE1)1モルに対して、還元剤が通常1〜30モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XB1)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method F)
Compound (XB1) can be produced by reacting compound (XE1) with a reducing agent in the presence of an acid.
[Wherein R 101 and E represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include aliphatic carboxylic acids such as acetic acid, alcohols such as methanol and ethanol, water, and mixtures thereof.
Examples of the reducing agent used in the reaction include iron, tin, and zinc.
Examples of the acid used in the reaction include hydrochloric acid, sulfuric acid, acetic acid, and an aqueous ammonium chloride solution.
In the reaction, the reducing agent is usually used in a proportion of 1 to 30 mol with respect to 1 mol of the compound (XE1).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XB1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法G)
式(XG2)で示される化合物(以下、化合物(XG2)と記す。)は、式(XG1)で示される化合物(以下、化合物(XG1)と記す。)と化合物(E1)とを塩基の存在下反応させることにより製造することができる。
〔式中、R5、XおよびEはと同じ意味を表し、R191はP11またはP12を表す。〕
該反応は、製造法Eに準じて実施することができる。(Reference production method G)
The compound represented by the formula (XG2) (hereinafter referred to as the compound (XG2)) is obtained by combining the compound represented by the formula (XG1) (hereinafter referred to as the compound (XG1)) with the compound (E1). It can manufacture by making it react.
[Wherein R 5 , X and E represent the same meaning as R 191 represents P 11 or P 12 . ]
The reaction can be carried out according to Production Method E.
(参考製造法H)
式(XH2)で示される化合物(以下、化合物(XH2)と記す。)は、式(XH1)で示される化合物(以下、化合物(XH1)と記す。)とハロゲン化剤とを反応させることにより製造することができる。
〔式中、RA1、RA2、E、R5、Z21およびXは前記と同じ意味を表し、R201はP51またはニトロ基を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、フルオロベンゼン、ジフルオロベンゼン、トリフルオロベンゼン、クロロベンゼン、ジクロロベンゼン、トリクロロベンゼン、α,α,α−トリフルオロトルエン、α,α,α−トリクロロトルエン等のハロゲン化炭化水素類、酢酸エチル、酢酸メチル等のエステル類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類およびこれらの混合物が挙げられる。
該反応に用いることができるハロゲン化剤としては、塩素化、臭素化もしくはヨウ素化剤、例えば塩素、臭素、ヨウ素、塩化スルフリル、N−クロロスクシンイミド、N−ブロモスクシンイミド、1,3−ジブロモ−5,5−ジメチルヒダントイン、ヨードスクシンイミド、次亜塩素酸tert−ブチル、N−クロログルタルイミド、N−ブロモグルタルイミド、N−クロロ−N−シクロヘキシル−ベンゼンスルホンイミド、N−ブロモフタルイミド等を挙げることができる。
該反応にはラジカル開始剤を用いることも出来る。
該反応に用いられるラジカル開始剤としては、過酸化ベンゾイル、アゾビスイソブチロニトリル(AIBN)、ジアシルペルオキシド、ジアルキルペルオキシジカルボネート、tert−アルキルペルオキシエステル、モノペルオキシカルボネート、ジ(tert−アルキルペルオキシ)ケタールおよびケトンペルオキシド等を挙げることができる。
該反応には化合物(XH1)1モルに対して、ハロゲン化剤が通常1〜10モルの割合、ラジカル開始剤は通常0.01〜5モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XH2)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method H)
A compound represented by formula (XH2) (hereinafter referred to as compound (XH2)) is obtained by reacting a compound represented by formula (XH1) (hereinafter referred to as compound (XH1)) with a halogenating agent. Can be manufactured.
[Wherein, R A1 , R A2 , E, R 5 , Z 21 and X represent the same meaning as described above, and R 201 represents P 51 or a nitro group. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ter, anisole, ethers such as methyl tert-butyl ether, diisopropyl ether, carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, fluorobenzene, difluorobenzene, trifluorobenzene, chlorobenzene, dichlorobenzene, trichlorobenzene , Α, α, α-trifluorotoluene, halogenated hydrocarbons such as α, α, α-trichlorotoluene, esters such as ethyl acetate and methyl acetate, acetone, methyl ethyl ketone, methyl Ketones such as isobutyl ketone, acetonitrile, nitriles and mixtures thereof, such as propionitrile and the like.
Examples of the halogenating agent that can be used in the reaction include chlorination, bromination or iodination agents such as chlorine, bromine, iodine, sulfuryl chloride, N-chlorosuccinimide, N-bromosuccinimide, 1,3-dibromo-5. , 5-dimethylhydantoin, iodosuccinimide, tert-butyl hypochlorite, N-chloroglutarimide, N-bromoglutarimide, N-chloro-N-cyclohexyl-benzenesulfonimide, N-bromophthalimide and the like. it can.
A radical initiator can also be used for this reaction.
The radical initiator used in the reaction includes benzoyl peroxide, azobisisobutyronitrile (AIBN), diacyl peroxide, dialkylperoxydicarbonate, tert-alkylperoxyester, monoperoxycarbonate, di (tert-alkylperoxy). ) Ketals and ketone peroxides.
In the reaction, the halogenating agent is usually used in a proportion of 1 to 10 mol and the radical initiator is usually used in a proportion of 0.01 to 5 mol with respect to 1 mol of the compound (XH1).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XH2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法I)
式(XJ2)で示される化合物(以下、化合物(XJ2)と記す。)は、化合物(XH2)と式(XJ1)で示される化合物(以下、化合物(XJ1)と記す。)とを反応させることにより製造することができる。
〔式中、RA1、RA2、E、R111、R201およびZ21は前記と同じ意味を表し、Mはナトリウム、カリウム、またはリチウムを表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエ−テル類、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、メタノール、エタノール、プロパノール、ブタノール等のアルコール類およびこれらの混合物が挙げられる。
該反応に用いることができる化合物(XJ1)としては、ナトリウムメトキシド、ナトリウムエトキシド、ナトリウムプロポキシド、ナトリウムブトキシド、ナトリウムイソプロポキシド、ナトリウムsec−ブトキシド、ナトリウムtert−ブトキシド、カリウムメトキシド、カリウムエトキシド、カリウムプロポキシド、カリウムブトキシド、カリウムイソプロポキシド、カリウムsec−ブトキシド、カリウムtert−ブトキシド、ナトリウムフェノキシド等が挙げられる。
該反応には化合物(XH2)1モルに対して、化合物(XJ1)が通常1〜10モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XJ2)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method I)
A compound represented by formula (XJ2) (hereinafter referred to as compound (XJ2)) is reacted with a compound (XH2) and a compound represented by formula (XJ1) (hereinafter referred to as compound (XJ1)). Can be manufactured.
[Wherein, R A1 , R A2 , E, R 111 , R 201 and Z 21 represent the same meaning as described above, and M represents sodium, potassium or lithium. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisole, methyl tert-butyl ether, diisopropyl ether, n-heptane, n -Hydrocarbons such as hexane, cyclohexane, n-pentane, toluene, xylene, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, acetonitrile, propionitrile, etc. Nitriles, N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl Ketones such as butyl ketone, methanol, ethanol, propanol, and mixtures thereof, such as butanol.
Examples of the compound (XJ1) that can be used in the reaction include sodium methoxide, sodium ethoxide, sodium propoxide, sodium butoxide, sodium isopropoxide, sodium sec-butoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxy. And potassium propoxide, potassium butoxide, potassium isopropoxide, potassium sec-butoxide, potassium tert-butoxide, sodium phenoxide and the like.
In the reaction, compound (XJ1) is usually used at a ratio of 1 to 10 mol per 1 mol of compound (XH2).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XJ2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法J)
式(XK1)で示される化合物(以下、化合物(XK1)と記す。)は、化合物(XH2)を塩基の存在下で水と反応させることにより製造することができる。
〔式中RA1、RA2、E、Z21およびR201は前記と同じ意味を表す。〕
該反応は、通常、水中もしくは、水を含む溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエ−テル類、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、メタノール、エタノール、プロパノール、ブタノール等のアルコール類およびこれらの混合物が挙げられる。
該反応に用いられる塩基としては、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、ギ酸リチウム、酢酸リチウム、ギ酸ナトリウム、酢酸ナトリウム、ギ酸カリウム、酢酸カリウム等の金属有機酸塩、硝酸銀、硝酸ナトリウム等の金属硝酸塩、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム等のアルカリ金属水酸化物、ナトリウムメトキシド、ナトリウムエトキシド、ナトリウムtert−ブトキシド、カリウムtert−ブトキシドのアルカリ金属アルコキシド等が挙げられる。
該反応には化合物(XH2)1モルに対して、塩基が通常1〜100モルの割合で用いられる。
該反応には化合物(XH2)1モルに対して、水が通常1モル〜大過剰の割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XK1)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method J)
A compound represented by the formula (XK1) (hereinafter referred to as compound (XK1)) can be produced by reacting compound (XH2) with water in the presence of a base.
[Wherein R A1 , R A2 , E, Z 21 and R 201 represent the same meaning as described above. ]
The reaction is usually performed in water or a solvent containing water.
Examples of the solvent used in the reaction include ethers such as diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether, anisole, methyl tert-butyl ether, diisopropyl ether, n-heptane, n -Hydrocarbons such as hexane, cyclohexane, n-pentane, toluene, xylene, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, acetonitrile, propionitrile, etc. Nitriles, N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl Ketones such as butyl ketone, methanol, ethanol, propanol, and mixtures thereof, such as butanol.
Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene. Metal organic acid salts such as lithium formate, lithium acetate, sodium formate, sodium acetate, potassium formate and potassium acetate, metal nitrates such as silver nitrate and sodium nitrate, alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate and cesium carbonate Salts, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, alkali metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, sodium metho Sid, sodium ethoxide, sodium tert- butoxide, alkali metal alkoxides such as potassium tert- butoxide.
In the reaction, the base is generally used at a ratio of 1 to 100 mol with respect to 1 mol of the compound (XH2).
In the reaction, water is usually used in a proportion of 1 mol to large excess with respect to 1 mol of compound (XH2).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XK1) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法K)
化合物(XH2)は、化合物(XJ2)とハロゲン化剤とを反応させることにより製造することができる。
〔式中、RA1、RA2、R111、R201、EおよびZ21は前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、ギ酸、酢酸、トリフルオロ酢酸等の有機酸類、水およびこれらの混合物が挙げられる。
該反応に用いられるハロゲン化剤としては、例えば、塩酸、臭化水素酸、およびヨウ化水素酸が挙げられる。
該反応には化合物(XJ2)1モルに対して、ハロゲン化剤が通常1モル以上の割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XH2)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method K)
Compound (XH2) can be produced by reacting compound (XJ2) with a halogenating agent.
[Wherein, R A1 , R A2 , R 111 , R 201 , E and Z 21 represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane. Halogenated hydrocarbons such as chlorobenzene, ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, organic acids such as formic acid, acetic acid and trifluoroacetic acid, water and mixtures thereof. Can be mentioned.
Examples of the halogenating agent used in the reaction include hydrochloric acid, hydrobromic acid, and hydroiodic acid.
In the reaction, the halogenating agent is usually used at a ratio of 1 mol or more per 1 mol of the compound (XJ2).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XH2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法L)
化合物(XH2)は、化合物(XK1)とハロゲン化剤とを反応させることにより製造することができる。
〔式中、RA1、RA2、R201、EおよびZ21は前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、酢酸エチル、酢酸メチル等のエステル類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、ギ酸、酢酸、トリフルオロ酢酸等の有機酸類、水およびこれらの混合物が挙げられる。
該反応に用いられるハロゲン化剤としては、例えば、臭素、塩素、塩化スルフリル、塩酸、臭化水素酸、ヨウ化水素酸、三臭化ホウ素、三臭化リン、塩化トリメチルシリル、臭化トリメチルシリル、ヨウ化トリメチルシリル、塩化チオニル、臭化チオニル、オキシ塩化リン、三塩化リン、五塩化リン、塩化チオニル、オキシ臭化リン、五臭化リン、三ヨウ化リン、二塩化オキサリル、二臭化オキサリル、塩化アセチル、四臭化炭素、N−ブロモスクシンイミド、塩化リチウム、ヨウ化ナトリウム、臭化アセチル等が挙げられる。
該反応には化合物(XK1)1モルに対して、ハロゲン化剤が通常1〜10モルの割合で用いられる。
該反応を進行させるため、使用するハロゲン化剤によっては添加剤を加える必要があり、具体的には、塩化アセチルに対する塩化亜鉛、四臭化炭素に対するトリフェニルホスフィン、N−ブロモスクシンイミドに対するジメチルスルフィド、ヨウ化ナトリウムに対する三フッ化ホウ素ジエチルエーテル錯体、臭化アセチルに対する三フッ化ホウ素ジエチルエーテル錯体、塩化リチウムに対するトリエチルアミン及び塩化メタンスルホニル、ヨウ化ナトリウムに対する塩化アルミニウム、ヨウ化ナトリウムに対する塩化トリメチルシリル等が挙げられる。その使用量はいずれの添加剤も、通常、化合物(XK1)1モルに対して、0.01〜5モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XH2)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method L)
Compound (XH2) can be produced by reacting compound (XK1) with a halogenating agent.
[Wherein, R A1 , R A2 , R 201 , E and Z 21 represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether and diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane and chlorobenzene, esters such as ethyl acetate and methyl acetate , Ketones such as acetone, methyl ethyl ketone and methyl isobutyl ketone, nitriles such as acetonitrile and propionitrile, organic acids such as formic acid, acetic acid and trifluoroacetic acid, water and mixtures thereof.
Examples of the halogenating agent used in the reaction include bromine, chlorine, sulfuryl chloride, hydrochloric acid, hydrobromic acid, hydroiodic acid, boron tribromide, phosphorus tribromide, trimethylsilyl chloride, trimethylsilyl bromide, iodine Trimethylsilyl chloride, thionyl chloride, thionyl bromide, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride, thionyl chloride, phosphorus oxybromide, phosphorus pentabromide, phosphorus triiodide, oxalyl dichloride, oxalyl dibromide, chloride Examples include acetyl, carbon tetrabromide, N-bromosuccinimide, lithium chloride, sodium iodide, acetyl bromide and the like.
In the reaction, the halogenating agent is generally used at a ratio of 1 to 10 moles relative to 1 mole of the compound (XK1).
In order to proceed with the reaction, it is necessary to add an additive depending on the halogenating agent used, specifically, zinc chloride for acetyl chloride, triphenylphosphine for carbon tetrabromide, dimethyl sulfide for N-bromosuccinimide, Boron trifluoride diethyl ether complex for sodium iodide, boron trifluoride diethyl ether complex for acetyl bromide, triethylamine and methanesulfonyl chloride for lithium chloride, aluminum chloride for sodium iodide, trimethylsilyl chloride for sodium iodide, etc. . As for the usage-amount, any additive is normally used in the ratio of 0.01-5 mol with respect to 1 mol of compounds (XK1).
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XH2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法M)
式(XM3)で示される化合物(以下、化合物(XM3)と記す。)は、化合物(XK1)と式(XM2)で示される一般に入手可能な化合物(以下、化合物(XM2)と記す。)とを塩基の存在下で反応させることにより製造することができる。
〔式中、RA1、RA2、EおよびR201は前記と同じ意味を表し、R901はC1−C6アルキル基、C1−C6ハロアルキル基、C6−C16アリール基、またはC6−C16ハロアリール基を表し、Z801はフッ素原子、塩素原子、臭素原子またはヨウ素原子を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、アセトニトリル、プロピオニトリル等のニトリル類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類及びこれらの混合物が挙げられる。
該反応に用いられる塩基としては、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム等のアルカリ金属水酸化物、水素化リチウム、水素化ナトリウム、水素化カリウム等のアルカリ金属水素化物、ナトリウムメトキシド、ナトリウムエトキシド、ナトリウムtert−ブトキシド、カリウムtert−ブトキシドのアルカリ金属アルコキシド等が挙げられる。
該反応には化合物(XK1)1モルに対して、化合物(XM2)が通常1〜10モルの割合、塩基が通常1〜5モルの割合で用いられる。
該反応の反応温度は通常−20〜150℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
該反応は、必要に応じてヨウ化ナトリウム、ヨウ化テトラブチルアンモニウムなどを加えてもよく、これらの化合物は通常、化合物(XK1)1モルに対して、0.001〜1.2モルの割合で用いられる。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XM3)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method M)
A compound represented by the formula (XM3) (hereinafter referred to as the compound (XM3)) is a compound (XK1) and a generally available compound represented by the formula (XM2) (hereinafter referred to as the compound (XM2)). Can be prepared by reacting in the presence of a base.
[Wherein, R A1 , R A2 , E and R 201 represent the same meaning as described above, and R 901 represents a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C6-C16 aryl group, or a C6-C16 haloaryl group. Z 801 represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as tellurium, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, nitriles such as acetonitrile, propionitrile, etc. N, N-dimethylformamide, 1,3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl Ketones such as butyl ketone and mixtures thereof.
Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene and diazabicyclononene. Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc., lithium hydroxide, sodium hydroxide, Alkali metal hydroxides such as potassium hydroxide and cesium hydroxide, lithium hydride, sodium hydride, alkali metal hydrides such as potassium hydride, sodium methoxide, sodium ethoxide, sodium tert-butoxide, potassium Alkali metal alkoxides such tert- butoxide.
In the reaction, with respect to 1 mol of the compound (XK1), the compound (XM2) is usually used in a proportion of 1 to 10 mol, and the base is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
In this reaction, sodium iodide, tetrabutylammonium iodide or the like may be added if necessary, and these compounds are usually in a ratio of 0.001 to 1.2 mol per 1 mol of compound (XK1). Used in
After completion of the reaction, the compound (XM3) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法N)
化合物(1)のうち、式(XN12)で示される化合物(以下、化合物(XN12)と記す。)は、式(XN11)で示される化合物(以下、化合物(XN11)と記す。)と式(G21)で示される化合物(以下、化合物(G21)と記す。)とを、塩基及び触媒存在下カップリング反応することにより製造することができる。
〔式中、R501はP11、P12、P61またはP62を表し、R5、R71、X、Z2、Z3、Z4、Z31およびZ41は前記と同じ意味を表す。R121はC1−C6アルキル基、C1−C6ハロアルキル基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C5アルコキシカルボニル基、C2−C5ハロアルコキシカルボニル基、ベンジル基またはベンゾイル基(但し、該ベンジル基またはベンゾイル基は、C1−C3アルキル基、C1−C3ハロアルキル基、ハロゲン原子、およびニトロ基からなる群より選ばれる基で置換されていてもよい。)を表す。ただし、Z2、Z3およびZ4のうち、少なくとも1つは窒素原子を表す。〕
該反応は、製造法Bに準じて実施することができる。(Reference production method N)
Among compounds (1), a compound represented by formula (XN12) (hereinafter referred to as compound (XN12)) is a compound represented by formula (XN11) (hereinafter referred to as compound (XN11)) and a formula ( A compound represented by G21) (hereinafter referred to as compound (G21)) can be produced by a coupling reaction in the presence of a base and a catalyst.
[Wherein R 501 represents P 11 , P 12 , P 61 or P 62 , and R 5 , R 71 , X, Z 2 , Z 3 , Z 4 , Z 31 and Z 41 represent the same meaning as described above. . R 121 is a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C2-C6 alkylcarbonyl group, a C2-C6 haloalkylcarbonyl group, a C2-C5 alkoxycarbonyl group, a C2-C5 haloalkoxycarbonyl group, a benzyl group or a benzoyl group ( However, the benzyl group or benzoyl group may be substituted with a group selected from the group consisting of a C1-C3 alkyl group, a C1-C3 haloalkyl group, a halogen atom, and a nitro group. However, at least one of Z 2 , Z 3 and Z 4 represents a nitrogen atom. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN22)で示される化合物(以下、化合物(XN22)と記す。)は、式(XN21)で示される化合物(以下、化合物(XN21)と記す。)と式(G22)で示される化合物(以下、化合物(G22)と記す。)とを塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、X、R5、Z1、Z3、Z4、Z31およびZ41は前記と同じ意味を表し、R72はC1−C3アルキル基を表す。ただし、Z1、Z3およびZ4のうち、少なくとも1つは窒素原子を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (XN22) (hereinafter referred to as compound (XN22)) is a compound represented by formula (XN21) (hereinafter referred to as compound (XN21)) and a formula ( It can be produced by subjecting a compound represented by G22) (hereinafter referred to as compound (G22)) to a coupling reaction in the presence of a base and a catalyst.
[Wherein, R 501 , X, R 5 , Z 1 , Z 3 , Z 4 , Z 31 and Z 41 represent the same meaning as described above, and R 72 represents a C1-C3 alkyl group. However, at least one of Z 1 , Z 3 and Z 4 represents a nitrogen atom. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN32)で示される化合物(以下、化合物(XN32)と記す。)は、式(XN31)で示される化合物(以下、化合物(XN31)と記す。)と化合物(G22)とを塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、X、R5、R72、Z1、Z2、Z4、Z31およびZ41は前記と同じ意味を表す。ただし、Z1、Z2およびZ4のうち、少なくとも1つは窒素原子を表す。〕
該反応は、製造法Bに準じて実施することができる。Among the compounds (1), a compound represented by formula (XN32) (hereinafter referred to as compound (XN32)) is a compound represented by formula (XN31) (hereinafter referred to as compound (XN31)) and a compound ( G22) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein, R 501 , X, R 5 , R 72 , Z 1 , Z 2 , Z 4 , Z 31 and Z 41 represent the same meaning as described above. However, at least one of Z 1 , Z 2 and Z 4 represents a nitrogen atom. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN42)で示される化合物(以下、化合物(XN42)と記す。)は、式(XN41)で示される化合物(以下、化合物(XN41)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、X、R5、R72、Z1、Z2、Z3、Z31およびZ41は前記と同じ意味を表す。ただし、Z1、Z2およびZ3のうち、少なくとも1つは窒素原子を表す。〕
該反応は、製造法Bに準じて実施することができる。Among the compounds (1), a compound represented by formula (XN42) (hereinafter referred to as compound (XN42)) is a compound represented by formula (XN41) (hereinafter referred to as compound (XN41)). (G22) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein, R 501 , X, R 5 , R 72 , Z 1 , Z 2 , Z 3 , Z 31 and Z 41 represent the same meaning as described above. However, at least one of Z 1 , Z 2 and Z 3 represents a nitrogen atom. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN52)で示される化合物(以下、化合物(XN52)と記す。)は、式(XN51)で示される化合物(以下、化合物(XN51)と記す。)とを化合物(G21)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、Y2、X、R5、R71、Z3、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among compounds (1), a compound represented by formula (XN52) (hereinafter referred to as compound (XN52)) is a compound represented by formula (XN51) (hereinafter referred to as compound (XN51)). (G21) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein R 501 , Y 2 , X, R 5 , R 71 , Z 3 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN62)で示される化合物(以下、化合物(XN62)と記す。)は、式(XN61)で示される化合物(以下、化合物(XN61)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、Y2、X、R5、R72、Z1、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among the compounds (1), a compound represented by formula (XN62) (hereinafter referred to as compound (XN62)) is a compound represented by formula (XN61) (hereinafter referred to as compound (XN61)). (G22) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein, R 501 , Y 2 , X, R 5 , R 72 , Z 1 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN72)で示される化合物(以下、化合物(XN72)と記す。)は、式(XN71)で示される化合物(以下、化合物(XN71)と記す。)とを化合物(G21)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、Y2、X、R5、R71、Z2、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among the compounds (1), a compound represented by formula (XN72) (hereinafter referred to as compound (XN72)) is a compound represented by formula (XN71) (hereinafter referred to as compound (XN71)). (G21) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein, R 501 , Y 2 , X, R 5 , R 71 , Z 2 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN82)で示される化合物(以下、化合物(XN82)と記す。)は、式(XN81)で示される化合物(以下、化合物(XN81)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、Y3、X、R5、R72、Z1、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among the compounds (1), a compound represented by formula (XN82) (hereinafter referred to as compound (XN82)) is a compound represented by formula (XN81) (hereinafter referred to as compound (XN81)). (G22) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein, R 501 , Y 3 , X, R 5 , R 72 , Z 1 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN92)で示される化合物(以下、化合物(XN92)と記す。)は、式(XN91)で示される化合物(以下、化合物(XN91)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、Y1、X、R5、R72、Z3、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among the compounds (1), a compound represented by the formula (XN92) (hereinafter referred to as the compound (XN92)) is a compound represented by the formula (XN91) (hereinafter referred to as the compound (XN91)). (G22) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein, R 501 , Y 1 , X, R 5 , R 72 , Z 3 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
化合物(1)のうち、式(XN102)で示される化合物(以下、化合物(XN102)と記す。)は、式(XN101)で示される化合物(以下、化合物(XN101)と記す。)とを化合物(G22)を塩基及び触媒存在下カップリング反応に供することにより製造することができる。
〔式中、R501、Y1、X、R5、R72、Z2、Z31およびZ41は前記と同じ意味を表す。〕
該反応は、製造法Bに準じて実施することができる。Among the compounds (1), a compound represented by the formula (XN102) (hereinafter referred to as compound (XN102)) is a compound represented by the formula (XN101) (hereinafter referred to as compound (XN101)). (G22) can be produced by subjecting it to a coupling reaction in the presence of a base and a catalyst.
[Wherein, R 501 , Y 1 , X, R 5 , R 72 , Z 2 , Z 31 and Z 41 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method B.
さらに、製造法Nに記載のカップリング反応に代えて、他の公知のカップリング反応を用いることにより、化合物(XN12)、化合物(XN32)、化合物(XN42)、化合物(XN52)、化合物(XN62)、化合物(XN72)、化合物(XN82)、化合物(XN92)および化合物(XN102)を製造することができる。 Furthermore, by using another known coupling reaction instead of the coupling reaction described in Production Method N, compound (XN12), compound (XN32), compound (XN42), compound (XN52), compound (XN62) ), Compound (XN72), compound (XN82), compound (XN92) and compound (XN102).
(参考製造法O)
式(XW2)で示される化合物(以下、化合物(XW2)と記す。)は、式(XW1)で示される化合物(以下、化合物(XW1)と記す。)を反応促進剤の存在下、式(XW3)で示される化合物(以下、化合物(XW3)と記す。)と反応させることにより製造することができる。
〔式中、EおよびR91は前記と同じ意味を表す。〕(Reference production method O)
A compound represented by the formula (XW2) (hereinafter referred to as the compound (XW2)) is a compound represented by the formula (XW1) (hereinafter referred to as the compound (XW1)) in the presence of a reaction accelerator. And XW3) (hereinafter referred to as compound (XW3)).
[Wherein, E and R 91 represent the same meaning as described above. ]
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類及びこれらの混合物があげられ、また、化合物(XW3)を溶媒として用いてもよい。
該反応に用いることができる化合物(XW3)としては、例えばメタノール、エタノール、プロピルアルコール、イソプロピルアルコール、n−ブチルアルコール、sec−ブチルアルコール、t−ブタノール、n−ペンタノール等があげられる。
該反応に用いられる反応促進剤としては、塩酸、硫酸等の鉱酸類、ジシクロヘキシルカルボジイミド、ジイソプロピルカルボジイミド、N’−(3−ジメチルアミノプロピル)−N−エチルカルボジイミド等のカルボジイミド、メタンスルホン酸、トルエンスルホン酸等の有機酸、トリフェニリルホスフィン/アゾジカルボン酸ジエチル等の光延反応試薬、塩化チオニル、ボロントリフルオリド−エチルエーテル コンプレックス等が挙げられる。
該反応には化合物(XW1)1モルに対して、反応促進剤が通常0.01〜10モルの割合で用いられる。
該反応は、必要に応じて、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩等を加えてもよく、これらの化合物は通常、化合物(XW1)1モルに対して、0.001〜5モルの割合で用いられる。
該反応には、化合物(XW1)に対して過剰量の化合物(XW3)を用いる。
該反応の反応温度は通常−78〜100℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XW2)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile and mixtures thereof, may also be used compound (XW3) as solvent.
Examples of the compound (XW3) that can be used in the reaction include methanol, ethanol, propyl alcohol, isopropyl alcohol, n-butyl alcohol, sec-butyl alcohol, t-butanol, and n-pentanol.
Examples of the reaction accelerator used in the reaction include mineral acids such as hydrochloric acid and sulfuric acid, carbodiimides such as dicyclohexylcarbodiimide, diisopropylcarbodiimide, N ′-(3-dimethylaminopropyl) -N-ethylcarbodiimide, methanesulfonic acid, and toluenesulfone. Examples thereof include organic acids such as acids, Mitsunobu reaction reagents such as triphenylylphosphine / diethyl azodicarboxylate, thionyl chloride, and boron trifluoride-ethyl ether complex.
In the reaction, the reaction accelerator is usually used in a proportion of 0.01 to 10 mol with respect to 1 mol of the compound (XW1).
The reaction may be carried out by using organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene, etc. , Alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal bicarbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, etc. The compound is usually used in a proportion of 0.001 to 5 mol with respect to 1 mol of compound (XW1).
In the reaction, an excess amount of the compound (XW3) is used with respect to the compound (XW1).
The reaction temperature of the reaction is usually in the range of −78 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XW2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法P)
化合物(XW2)は、化合物(XW1)とハロゲン化剤とを反応させ、式(XV1)で示される化合物(以下、化合物(XV1)と記す。)を得た後、化合物(XV1)と化合物(XW3)とを反応させることにより製造することができる。
〔式中、E、R91およびZ101は前記と同じ意味を表す。〕
化合物(XW1)とハロゲン化剤とを反応させ化合物(XV1)を製造する方法は、参考製造法Cに準じて実施することができる。(Reference production method P)
Compound (XW2) is obtained by reacting compound (XW1) with a halogenating agent to obtain a compound represented by formula (XV1) (hereinafter referred to as compound (XV1)), and then compound (XV1) and compound (XV1). XW3) can be reacted.
[Wherein, E, R 91 and Z 101 represent the same meaning as described above. ]
The method for producing compound (XV1) by reacting compound (XW1) with a halogenating agent can be carried out according to Reference Production Method C.
以下に化合物(XV1)から化合物(XW2)を製造する方法について説明する。
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類及びこれらの混合物があげられ、化合物(XW3)を溶媒として用いてもよい。
該反応に用いることができる化合物(XW3)としては、参考製造法Oに記載の化合物が挙げられる。
該反応には、化合物(XV1)に対して、過剰量の化合物(XW3)を用いる。
該反応の反応温度は通常−78〜100℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XW2)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。The method for producing compound (XW2) from compound (XV1) is described below.
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, and mixtures thereof and the like, may be used compound (XW3) as solvent.
Examples of the compound (XW3) that can be used in the reaction include compounds described in Reference Production Method O.
In the reaction, an excess amount of the compound (XW3) is used with respect to the compound (XV1).
The reaction temperature of the reaction is usually in the range of −78 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XW2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法Q)
化合物(XW2)は、化合物(XW1)とアルキル化剤とを反応させることにより製造することができる。
〔式中、EおよびR91は前記と同じ意味を表す。〕
該反応は、通常溶媒中で行われる。
該反応に用いられる溶媒としては、例えば、n−ヘプタン、n−ヘキサン、シクロヘキサン、n−ペンタン、トルエン、キシレン等の炭化水素類、ジエチルエーテル、テトラヒドロフラン、1,4−ジオキサン、エチレングリコ−ルジメチルエ−テル、アニソール、メチルtert−ブチルエーテル、ジイソプロピルエーテル等のエーテル類、四塩化炭素、クロロホルム、ジクロロメタン、1,2−ジクロロエタン、テトラクロロエタン、クロロベンゼン等のハロゲン化炭化水素類、N,N−ジメチルホルムアミド、1,3−ジメチル−2−イミダゾリジノン、N−メチルピロリドン等の酸アミド類、酢酸エチル、酢酸メチル等のエステル類、ジメチルスルホキシド等のスルホキシド類、アセトン、メチルエチルケトン、メチルイソブチルケトン等のケトン類、アセトニトリル、プロピオニトリル等のニトリル類、水およびこれらの混合物が挙げられる。
該反応に用いることができるアルキル化剤としては、例えばジアゾメタン、トリメチルシリルジアゾメタン、臭化メチル、臭化エチル、臭化プロピル、ヨウ化メチル、ヨウ化エチル、ヨウ化プロピル等のハロゲン化アルキル類、硫酸ジメチル、硫酸ジエチル、硫酸ジプロピル等の硫酸ジアルキル類、p−トルエンスルホン酸メチル、p−トルエンスルホン酸エチル、p−トルエンスルホン酸プロピル、メタンスルホン酸メチル、メタンスルホン酸エチル、メタンスルホン酸n−プロピル等のアルキルまたはアリールスルホン酸エステル類等を挙げることができる。
該反応には化合物(XW1)1モルに対して、アルキル化剤が通常1〜10モルの割合で用いられる。
該反応は、必要に応じて、トリエチルアミン、ピリジン、N−メチルモルホリン、N−メチルピペリジン、4−ジメチルアミノピリジン、ジイソプロピルエチルアミン、ルチジン、コリジン、ジアザビシクロウンデセン、ジアザビシクロノネン等の有機塩基、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等のアルカリ金属炭酸塩、炭酸水素リチウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸水素セシウム等のアルカリ金属炭酸水素塩、テトラブチルアンモニウムヒドロキシド等の4級アンモニウム塩等を加えてもよく、これらの化合物は通常、化合物(XW1)1モルに対して、0.001〜5モルの割合で用いられる。
該反応の反応温度は通常−78〜100℃の範囲である。該反応の反応時間は通常0.1〜24時間の範囲である。
反応終了後は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、化合物(XW2)を単離することができる。さらに蒸留、クロマトグラフィー、再結晶等の操作で精製してもよい。(Reference production method Q)
Compound (XW2) can be produced by reacting compound (XW1) with an alkylating agent.
[Wherein, E and R 91 represent the same meaning as described above. ]
The reaction is usually performed in a solvent.
Examples of the solvent used in the reaction include hydrocarbons such as n-heptane, n-hexane, cyclohexane, n-pentane, toluene, xylene, diethyl ether, tetrahydrofuran, 1,4-dioxane, ethylene glycol dimethyl ether. Ethers such as ter, anisole, methyl tert-butyl ether, diisopropyl ether, halogenated hydrocarbons such as carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, tetrachloroethane, chlorobenzene, N, N-dimethylformamide, 1 , 3-dimethyl-2-imidazolidinone, acid amides such as N-methylpyrrolidone, esters such as ethyl acetate and methyl acetate, sulfoxides such as dimethyl sulfoxide, acetone, methyl ethyl ketone, methyl isobutyl ketone Ketones such as down, nitriles such as acetonitrile and propionitrile, water and mixtures thereof.
Examples of the alkylating agent that can be used in the reaction include alkyl halides such as diazomethane, trimethylsilyldiazomethane, methyl bromide, ethyl bromide, propyl bromide, methyl iodide, ethyl iodide, propyl iodide, and sulfuric acid. Dialkyl sulfates such as dimethyl, diethyl sulfate and dipropyl sulfate, methyl p-toluenesulfonate, ethyl p-toluenesulfonate, propyl p-toluenesulfonate, methyl methanesulfonate, ethyl methanesulfonate, n-propyl methanesulfonate Alkyl or aryl sulfonic acid esters such as
In the reaction, the alkylating agent is usually used at a ratio of 1 to 10 moles relative to 1 mole of the compound (XW1).
The reaction may be carried out by using organic bases such as triethylamine, pyridine, N-methylmorpholine, N-methylpiperidine, 4-dimethylaminopyridine, diisopropylethylamine, lutidine, collidine, diazabicycloundecene, diazabicyclononene, etc. 4 such as alkali metal carbonates such as lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, alkali metal hydrogen carbonates such as lithium hydrogen carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium hydrogen carbonate, tetrabutylammonium hydroxide, etc. A quaternary ammonium salt or the like may be added, and these compounds are usually used in a proportion of 0.001 to 5 mol with respect to 1 mol of the compound (XW1).
The reaction temperature of the reaction is usually in the range of −78 to 100 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound (XW2) can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. Further, purification may be performed by operations such as distillation, chromatography, recrystallization and the like.
(参考製造法T)
式(XS2)で示される化合物(以下、化合物(XS2)と記す。)は、式(XS1)で示される化合物(以下、化合物(XS1)と記す。)と化合物(A2)とを塩基の存在下で反応させることにより製造することができる。
〔式中、RA1、RA2、G、E、A、QおよびZ11は前記と同じ意味を表す。〕
該反応は、製造法Aに準じて実施することができる。(Reference production method T)
The compound represented by the formula (XS2) (hereinafter referred to as the compound (XS2)) is obtained by combining the compound represented by the formula (XS1) (hereinafter referred to as the compound (XS1)) with the compound (A2). It can manufacture by making it react under.
[Wherein, R A1 , R A2 , G, E, A, Q and Z 11 represent the same meaning as described above. ]
The reaction can be carried out according to Production Method A.
本発明化合物が使用される形態としては、本発明化合物単独であってもよいが、通常は本発明化合物を、固体担体、液体担体、界面活性剤等と混合し、必要により固着剤、分散剤、安定剤等の製剤用補助剤を添加して、水和剤、顆粒水和剤、フロアブル剤、粒剤、ドライフロアブル剤、乳剤、水性液剤、油剤、くん煙剤、エアゾ−ル剤、マイクロカプセル剤等に製剤化して用いる。これらの製剤には本発明化合物が重量比で通常0.1〜99%、好ましくは0.2〜90%含有される。 The form of the compound of the present invention may be the compound of the present invention alone. Usually, the compound of the present invention is mixed with a solid carrier, a liquid carrier, a surfactant, etc., and if necessary, a fixing agent or a dispersing agent. Additives for preparations such as stabilizers, wettable powder, granular wettable powder, flowable powder, granules, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol, micro It is used in the form of capsules. These preparations usually contain 0.1 to 99%, preferably 0.2 to 90% by weight of the compound of the present invention.
固体担体としては、例えば、粘土類(例えば、カオリン、珪藻土、合成含水酸化珪素、フバサミクレー、ベントナイト、酸性白土)、タルク類、その他の無機鉱物(例えば、セリサイト、石英粉末、硫黄粉末、活性炭、炭酸カルシウム、水和シリカ)等の微粉末あるいは粒状物が挙げられ、液体担体としては、例えば、水、アルコ−ル類(例えば、メタノ−ル、エタノ−ル)、ケトン類(例えば、アセトン、メチルエチルケトン)、芳香族炭化水素類(例えば、ベンゼン、トルエン、キシレン、エチルベンゼン、メチルナフタレン)、脂肪族炭化水素類(例えば、n−ヘキサン、シクロヘキサノン、灯油)、エステル類(例えば、酢酸エチル、酢酸ブチル)、ニトリル類(例えば、アセトニトリル、イソブチロニトリル)、エ−テル類(例えば、ジオキサン、ジイソプロピルエ−テル)、酸アミド類(例えば、DMF、ジメチルアセトアミド)、ハロゲン化炭化水素類(例えば、ジクロロエタン、トリクロロエチレン、四塩化炭素)が挙げられる。 Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples of the liquid carrier include water, alcohols (e.g., methanol, ethanol), ketones (e.g., acetone, Methyl ethyl ketone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexanone, kerosene), esters (eg, ethyl acetate, butyl acetate) ), Nitriles (eg acetonitrile, isobutyronitrile), ethers (eg , Dioxane, diisopropyl d - ether), acid amides (e.g., DMF, dimethylacetamide), halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, carbon tetrachloride) and the like.
界面活性剤としては、例えばアルキル硫酸エステル類、アルキルスルホン酸塩、アルキルアリ−ルスルホン酸塩、アルキルアリ−ルエ−テル類及びそのポリオキシエチレン化物、ポリオキシエチレングリコ−ルエ−テル類、多価アルコ−ルエステル類、糖アルコ−ル誘導体が挙げられる。 Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyvalent Examples include alcohol esters and sugar alcohol derivatives.
その他の製剤用補助剤としては、例えば固着剤や分散剤、具体的にはカゼイン、ゼラチン、多糖類(例えば、デンプン、アラビヤガム、セルロ−ス誘導体、アルギン酸)、リグニン誘導体、ベントナイト、糖類、合成水溶性高分子(例えば、ポリビニルアルコ−ル、ポリビニルピロリドン、ポリアクリル酸類)、PAP(酸性りん酸イソプロピル)、BHT(2,6−ジ−tert−ブチル−4−メチルフェノ−ル)、BHA(2−tert−ブチル−4−メトキシフェノ−ルと3−tert−ブチル−4−メトキシフェノ−ルとの混合物)、植物油、鉱物油、脂肪酸又はそのエステル等が挙げられる。 Other formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water solutions. Polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2- and a mixture of tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.
本発明防除剤を施用する方法としては、実質的に本発明防除剤が施用され得る形態であればその方法は特に限定されないが、例えば茎葉散布等の植物体への処理、土壌処理等の植物の栽培地への処理、種子消毒等の種子への処理等が挙げられる。
また、本発明防除剤は、鉱物油、植物油などの各種オイル、または界面活性剤等と混合して用いてもよい。具体的に混合して用いることができるオイル、界面活性剤としてはNimbus(登録商標)、Assist(登録商標)、Aureo(登録商標)、Iharol(登録商標)、Silwet L−77(登録商標)、BreakThru(登録商標)、SundanceII(登録商標)、Induce(登録商標)、Penetrator(登録商標)、AgriDex(登録商標)、Lutensol A8(登録商標)、NP−7(登録商標)、Triton(登録商標)、Nufilm(登録商標)、Emulgator NP7(登録商標)、Emulad(登録商標)、TRITON X 45(登録商標)、AGRAL 90(登録商標)、AGROTIN(登録商標)、ARPON(登録商標)、EnSprayN(登録商標)、BANOLE(登録商標)などが挙げられる。The method of applying the control agent of the present invention is not particularly limited as long as the control agent of the present invention can be applied substantially, but for example, treatment to plant bodies such as foliage spraying, plant such as soil treatment, etc. And the like, and the treatment of seeds such as seed disinfection.
Moreover, you may use this invention control agent in mixture with various oils, such as mineral oil and vegetable oil, or surfactant. Oils that can be used specifically mixed, surfactants include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark) , Nufilm (registered trademark), Emulator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark) Trademark) And the like BANOLE (registered trademark).
本発明防除剤の施用量は、気象条件、製剤形態、施用時期、施用方法、施用場所、対象病害、対象作物等によっても異なるが、本発明防除剤中の本発明化合物量で1000m2あたり、通常1〜500g、好ましくは2〜200gである。乳剤、水和剤、懸濁剤等は通常水で希釈して施用されるが、その場合の希釈後の本発明化合物濃度は、通常0.0005〜2重量%、好ましくは0.005〜1重量%であり、粉剤、粒剤等は通常希釈することなくそのまま施用される。種子への処理においては、種子1Kgに対して本発明防除剤中の本発明化合物量で、通常0.001〜100g、好ましくは0.01〜50gの範囲で施用される。
本発明防除剤は、畑、水田、芝生、果樹園等の農耕地における有害生物の防除剤として使用することができる。本発明防除剤は、以下に挙げられる「植物」等を栽培する農耕地等において、当該農耕地の病害を防除することができる。The application amount of the present control agent varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc., but the amount of the present compound in the present control agent per 1000 m 2 , Usually 1 to 500 g, preferably 2 to 200 g. Emulsions, wettable powders, suspensions and the like are usually diluted with water and applied. In this case, the concentration of the compound of the present invention after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to 1. The powder, granules and the like are usually applied as they are without dilution. In the seed treatment, the amount of the compound of the present invention in the control agent of the present invention is usually 0.001 to 100 g, preferably 0.01 to 50 g per 1 kg seed.
The control agent of the present invention can be used as a pest control agent in agricultural land such as fields, paddy fields, lawns, orchards. The control agent of the present invention can control diseases of the farmland in the farmland where the “plants” and the like listed below are cultivated.
また別の態様として、例えば、本発明化合物を上記した脊椎動物の内部(体内)あるいは外部(体表面)に投与することにより該脊椎動物に寄生する生物や寄生虫を全身的あるいは非全身的に駆除することができる。かかる内部投与の方法としては、経口投与、肛門投与、移植、注射による皮下・筋肉内・静脈投与が挙げられる。また、外部投与としては、経皮投与があげられる。また、家畜動物に摂食させて、その動物の排泄物に発生する衛生害虫を駆除することができる。
本発明化合物を、有害生物の寄生する家畜やペット等の動物に対して処理する場合、その投与量は、投与方法等に応じて広範囲に変えることができるが、一般的には、動物体重1kg当たりの有効成分(本発明化合物またはその塩)が0.1mg〜2000mg、好ましくは0.5mg〜1000mgとなるように投与することが望ましい。In another embodiment, for example, by administering the compound of the present invention to the inside (in the body) or outside (the body surface) of the vertebrate, the organism or parasite that parasitizes the vertebrate is systemically or non-systemically. Can be disinfected. Examples of such internal administration include oral administration, anal administration, transplantation, subcutaneous, intramuscular and intravenous administration by injection. External administration includes transdermal administration. Moreover, it is possible to feed domestic animals and control sanitary pests generated in the excrement of the animals.
When the compound of the present invention is treated on animals such as livestock and pets that are parasitized with pests, the dosage can be varied widely depending on the administration method, etc. It is desirable to administer the active ingredient (the compound of the present invention or a salt thereof) at a concentration of 0.1 mg to 2000 mg, preferably 0.5 mg to 1000 mg.
本発明化合物は、畑、水田、芝生、果樹園等の農耕地における有害生物の防除剤として使用することができる。本発明化合物は、以下に挙げられる「植物」等を栽培する農耕地等において、当該農耕地の病害を防除することができる。
農作物;トウモロコシ、イネ、コムギ、オオムギ、ライムギ、エンバク、ソルガム、ワタ、ダイズ、ピ−ナッツ、ソバ、テンサイ、ナタネ、ヒマワリ、サトウキビ、タバコ等、野菜;ナス科野菜(ナス、トマト、ピ−マン、トウガラシ、ジャガイモ等)、ウリ科野菜(キュウリ、カボチャ、ズッキ−ニ、スイカ、メロン等)、アブラナ科野菜(ダイコン、カブ、セイヨウワサビ、コ−ルラビ、ハクサイ、キャベツ、カラシナ、ブロッコリー、カリフラワー等)、キク科野菜(ゴボウ、シュンギク、ア−ティチョ−ク、レタス等)、ユリ科野菜(ネギ、タマネギ、ニンニク、アスパラガス)、セリ科野菜(ニンジン、パセリ、セロリ、アメリカボウフウ等)、アカザ科野菜(ホウレンソウ、フダンソウ等)、シソ科野菜(シソ、ミント、バジル等)、イチゴ、サツマイモ、ヤマノイモ、サトイモ等、花卉、観葉植物、
果樹;仁果類(リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等)、核果類(モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プル−ン等)、カンキツ類(ウンシュウミカン、オレンジ、レモン、ライム、グレ−プフル−ツ等)、堅果類(クリ、クルミ、ハシバミ、ア−モンド、ピスタチオ、カシュ−ナッツ、マカダミアナッツ等)、液果類(ブル−ベリー、クランベリー、ブラックベリー、ラズベリー等)、ブドウ、カキ、オリ−ブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ等、
果樹以外の樹;チャ、クワ、花木、街路樹(トネリコ、カバノキ、ハナミズキ、ユ−カリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ)等。
上記「植物」には遺伝子組換え作物も含まれる。The compound of the present invention can be used as a pest control agent in agricultural land such as fields, paddy fields, lawns, orchards. The compound of the present invention can control diseases of the cultivated land in the cultivated lands where the “plants” and the like listed below are cultivated.
Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc., vegetables; solanaceous vegetables (eggplants, tomatoes, peppers) , Peppers, potatoes, etc.), cucurbitaceae vegetables (cucumber, pumpkin, zucchini, watermelon, melon, etc.), cruciferous vegetables (radish, turnip, horseradish, cold rabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc. ), Asteraceae vegetables (burdock, garlic, artichoke, lettuce, etc.), Liliaceae vegetables (green onion, onion, garlic, asparagus), Aceraceae vegetables (carrot, parsley, celery, American red pepper, etc.), Akaza Vegetables (spinach, chard, etc.), perilla vegetables (perilla, mint, basil) ), Strawberry, sweet potato, yam, taro, etc., flowers, foliage plants,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prune, etc.), citrus fruits (Satsuma mandarin, orange, lemon, lime) , Grapefruit, etc.), nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), Grape, oyster, olive, loquat, banana, coffee, date palm, coconut palm, etc.
Trees other than fruit trees; tea, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, tsuga, rat, Pine, spruce, yew).
The “plant” includes genetically modified crops.
本発明化合物により防除することができる有害生物としては、例えば糸状菌等の植物病原菌、並びに、有害昆虫類や有害ダニ類等の有害節足動物、およびセンチュウ類などの線形動物が挙げられ、より詳しくは以下のものを挙げることができるが、これらに限定されるものではない。
イネのいもち病(Magnaporthe grisea)、ごま葉枯病(Cochliobolus miyabeanus)、紋枯病(Rhizoctonia solani)、馬鹿苗病(Gibberella fujikuroi)、黄化萎縮病(Sclerophthora macrospora);コムギのうどんこ病(Erysiphe graminis)、赤かび病(Fusarium graminearum、F. avenaceum、F. culmorum、Microdochium nivale)、さび病(Puccinia striiformis、P. graminis、P. recondita)、紅色雪腐病(Micronectriella nivale)、雪腐小粒菌核病(Typhula sp.)、裸黒穂病(Ustilago tritici)、なまぐさ黒穂病(Tilletia caries,T.controversa)、眼紋病(Pseudocercosporella herpotrichoides)、葉枯病(Septoria tritici)、ふ枯病(Stagonospora nodorum)、黄斑病(Pyrenophora tritici−repentis)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani)、立枯病(Gaeumannomyces graminis);オオムギのうどんこ病(Erysiphe graminis)、赤かび病(Fusarium graminearum、F. avenaceum、F. culmorum、Microdochium nivale)、さび病(Puccinia striiformis、P.graminis、P.hordei)、裸黒穂病(Ustilago nuda)、雲形病(Rhynchosporium secalis)、網斑病(Pyrenophora teres)、斑点病(Cochliobolus sativus)、斑葉病(Pyrenophora graminea)、ラムラリア病(Ramularia collo−cygni)、リゾクトニア属菌による苗立枯れ病(Rhizoctonia solani);トウモロコシのさび病(Puccinia sorghi)、南方さび病(Puccinia polysora)、すす紋病(Setosphaeria turcica)、ごま葉枯病(Cochliobolus heterostrophus)、炭そ病(Colletotrichum graminicola)、グレーリーフスポット病(Cercospora zeae−maydis)、褐斑病(Kabatiella zeae)、ファエオスファエリアリーフスポット病(Phaeosphaeria maydis);ワタの炭そ病(Colletotrichum gossypii)、白かび病(Ramuraria areola)、黒斑病(Alternaria macrospora,A.gossypii);Examples of pests that can be controlled by the compounds of the present invention include phytopathogenic fungi such as filamentous fungi, harmful arthropods such as harmful insects and harmful ticks, and linear animals such as nematodes, The following can be mentioned in detail, but is not limited to these.
Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiotic seedling (Gibberella fujikuroi), yellow rot Graminis), Fusarium Graminearum, F. avenaceum, F. culmorum, Microdochium nivare, Rust (Puccinia striformis), P. graminis, P. reconditis Nuclear disease (Typhula sp. , Naked scab (Ustilago tritici), Tuna scab (Tilletia caries, T. controversa), eye spot disease (Pseudocercosporella herpotrichoides), leaf blight (Septoria tritium) -Repentis, Rhizotonia solani, Blight (Gaeumanomyces graminis); Barley powdery mildew (Erysipheumuminum, Fusarium magnum. Fusarium var.). Microdo Him nivale, rust disease (Puccinia striiformis, P. graminis, P. hordei), naked smut (Ustylago nuda), cloud disease (Rhynchosporis saris), reticulophor spot (Pyrephorphor spot) Leaf disease (Pyrenophora graminea), Ramularia disease (Ramularia collo-cygni), Rhizoctonia sorghum (Puccinia sorghi), psoriasis disease Setosphaeria turica), sesame leaf blight (Cochli) oboleus heterotrophus, anthracnose (Colletotrichum graminicola), gray leaf spot disease (Cercospora zeae-maydis), brown spot disease (Kabatiella zeaerum) disease, Phaeosfarea leaf disease gossypii), mildew (Ramuraria areola), black spot (Alternaria macrospora, A.). gossypii);
コーヒーのさび病(Hemileia vastatrix);ナタネの菌核病(Sclerotinia sclerotiorum)、黒斑病(Alternaria brassicae)、根朽病(Phoma lingam);カンキツ類の黒点病(Diaporthe citri)、そうか病(Elsinoe fawcetti)、果実腐敗病(Penicillium digitatum, P. italicum);リンゴのモニリア病(Monilinia mali)、腐らん病(Valsa ceratosperma)、うどんこ病(Podosphaera leucotricha)、斑点落葉病(Alternaria alternata apple pathotype)、黒星病(Venturia inaequalis)、炭そ病(Glomerella cingulata);ナシの黒星病(Venturia nashicola, V. pirina)、黒斑病(Alternaria alternata Japanese pear pathotype)、赤星病(Gymnosporangium haraeanum);モモの灰星病(Monilinia fructicola)、黒星病(Cladosporium carpophilum)、フォモプシス腐敗病(Phomopsis sp.);ブドウの黒とう病(Elsinoe ampelina)、晩腐病(Glomerella cingulata)、うどんこ病(Uncinulanecator)、さび病(Phakopsora ampelopsidis)、ブラックロット病(Guignardia bidwellii)、べと病(Plasmopara viticola);カキの炭そ病(Gloeosporium kaki)、落葉病(Cercospora kaki, Mycosphaerella nawae);ウリ類の炭そ病(Colletotrichum lagenarium)、うどんこ病(Sphaerotheca fuliginea)、つる枯病(Didymella bryoniae)、褐斑病(Coryncspora cassiicola)、つる割病(Fusarium oxysporum)、べと病(Pseudoperonospora cubensis)、疫病(Phytophthora sp.)、苗立枯病(Pythium sp.); Rust of coffee (Hemileia vastatrix); Sclerotinia sclerotia of rapeseed, black spot (Alternaria brassicae), phoenosis of citrus (Diapoetia, diapoetia) ), Fruit rot (Penicillium digitatum, P. italicum); apple monilia (Monilinia mali), rot (Valsa ceratosperma), powdery mildew (Podophaera leukotria), spotted leaf disease, Alptera terpata. (Venturia naequalis), anthracnose (Glomerella cingulata); pear black scab (Venturia nashiticola, V. pirina), black spot (Alternaria alternaum anemuumum) ), Black scab (Cladosporium carpophilum), pomopsis spoilage (Phomopsis sp.); Grape black scab (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinulaporpick) sidis, black lot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kakii), deciduous leaf disease (Cercospora kakii, Mycosphaerellato) Powdery mildew (Sphaerotheca furiginea), Vine blight (Didymella bryoniae), Brown spot (Corynspora casiicola), Vine split disease (Fusarium oxysporum), Downy mildew (Pseudosoporhos disease) ), Seedling blight (Pythium sp.);
トマトの輪紋病(Alternaria solani)、葉かび病(Cladosporium fulvum)、すすかび病(Pseudocercospora fuligena)、疫病(Phytophthora infestans);ナスの褐紋病(Phomopsis vexans)、うどんこ病(Erysiphecichoracearum);アブラナ科野菜の黒斑病(Alternaria japonica)、白斑病(Cercosporella brassicae)、根こぶ病(Plasmodiophora brassicae)、べと病(Peronospora parasitica);ネギのさび病(Puccinia allii);ダイズの紫斑病(Cercospora kikuchii)、黒とう病(Elsinoe glycines)、黒点病(Diaporthe phaseolorum var. sojae)、さび病(Phakopsora pachyrhizi)、褐色輪紋病(Corynespora cassiicola)、炭疽病(Colletotrithum glycines、C.truncatum)、葉腐病(Rhizoctonia solani)、褐紋病(Septoria glycines)、斑点病(Cercospora sojina);インゲンの炭そ病(Colletotrichum lindemthianum);ラッカセイの黒渋病(Cercospora personata)、褐斑病(Cercospora arachidicola)、白絹病(Sclerotium rolfsii);エンドウのうどんこ病(Erysiphe pisi);ジャガイモの夏疫病(Alternaria solani)、疫病(Phytophthora infestans)、半身萎凋病(Verticillium albo−atrum, V. dahliae, V. nigrescens);イチゴのうどんこ病(Sphaerotheca humuli);チャの網もち病(Exobasidium reticulatum)、白星病(Elsinoe leucospila)、輪斑病(Pestalotiopsis sp.)、炭そ病(Colletotrichum theae−sinensis);タバコの赤星病(Alternaria longipes)、うどんこ病(Erysiphe cichoracearum)、炭そ病(Colletotrichum tabacum)、べと病(Peronospora tabacina)、疫病(Phytophthora nicotianae);テンサイの褐斑病(Cercosporabeticola)、葉腐病(Thanatephorus cucumeris)、根腐病(Thanatephorus cucumeris)、黒根病(Aphanomyces cochlioides);バラの黒星病(Diplocarpon rosae)、うどんこ病(Sphaerotheca pannosa);キクの褐斑病(Septoria chrysanthemi−indici)、白さび病(Puccinia horiana);タマネギの白斑葉枯病(Botrytis cinerea, B. byssoidea, B. squamosa)、灰色腐敗病(Botrytis alli)、小菌核性腐敗病(Botrytis squamosa);種々の作物の灰色かび病(Botrytis cinerea)、菌核病(Sclerotinia sclerotiorum);ダイコン黒斑病(Alternaria brassicicola);シバのダラ−スポット病(Sclerotinia homeocarpa);シバのブラウンパッチ病およびラ−ジパッチ病(Rhizoctonia solani);並びにバナナのシガトカ病(Mycosphaerella fijiensis、Mycosphaerella musicola)。 Ring rot of tomato (Alternaria solani), leaf mold (Cladosporium fulvum), scab (Pseudocercospora fuligena), plague (Phytophorhora infestans); Black spot disease (Alternaria japonica), white spot disease (Cercosporella brassicae), root-knot disease (Plasmodiophora brassicae), downy mildew (Peronospora parasitica); i), black pepper (Elsinoe glycines), sunspot disease (Diaporthe phaseolum var. sojae), rust (Phokopsora pachyritolici), brown ring disease (Corynespora citalico citrus circo). Disease (Rhizoctonia solani), brown leaf disease (Septoria glycines), spot disease (Cercospora sojina); bean anthracnose (Colletotrichum colcoor cercospor disease) Silk disease (S pea powdery mildew (Erysiphe pisii); potato summer blight (Alternaria solani), blight (Phytophthora infestans, Strawberry varieties), Verticillium albodrum. Sphaerotheca humuli; Chamodium rot (Exobasidium reticulatum), white scab (Elsinoe leucospila), ring spot (Pestalotisis pneumoniae), and anthracnose (Colletotrichuminthae) ), Udon Diseases (Erysiphe cichoracerum), Anthracnose (Colletotrichum tabacum), Downy mildew (Peronosporata tabacumina), Blight (Phytophthora nichotiana leaf) (Cercosporacetic leaf disease) cucumeris, black root disease (Aphanomyces cochlioides); rose black spot disease (Diplocarpon rosae); powdery mildew (Sphaerotheca pannosain); Blight of onion (Botrytis cinerea, B .; byssoidea, B.M. squamosa), gray rot (Botrytis alli), small sclerotia rot (Botrytis squamosa); various crops of gray rot (Bottrytis cinereaol), sclerotia sclerotia varieties (Sclerotinia sclerotia) Shiva dara-spot disease (Sclerotinia homeocarpa); Shiba brown patch disease and radipatch disease (Rhizotonia solani);
半翅目害虫:ヒメトビウンカ(Laodelphax striatellus)、トビイロウンカ(Nilaparvata lugens)、セジロウンカ(Sogatella furcifera)等のウンカ類、ツマグロヨコバイ(Nephotettix cincticeps)、タイワンツマグロヨコバイ(Nephotettix virescens)等のヨコバイ類、ワタアブラムシ(Aphis gossypii)、モモアカアブラムシ(Myzus persicae)、ダイコンアブラムシ(Brevicoryne brassicae)、チューリップヒゲナガアブラムシ(Macrosiphum euphorbiae)、ジャガイモヒゲナガアブラムシ(Aulacorthum solani)、ムギクビレアブラムシ(Rhopalosiphum padi)、ミカンクロアブラムシ(Toxoptera citricidus)等のアブラムシ類、アオクサカメムシ(Nezara antennata)、ホソヘリカメムシ(Riptortus clavetus)、クモヘリカメムシ(Leptocorisa chinensis)、トゲシラホシカメムシ(Eysarcoris parvus)、クサギカメムシ(Halyomorpha mista)、ターニッシュドプラントバグ(Lygus lineolaris)等のカメムシ類、オンシツコナジラミ(Trialeurodes vaporariorum)、シルバーリーフコナジラミ(Bemisia argentifolii)等のコナジラミ類、アカマルカイガラムシ(Aonidiella aurantii)、サンホーゼカイガラムシ(Comstockaspis perniciosa)、シトラススノースケール(Unaspis citri)、ルビーロウムシ(Ceroplastes rubens)、イセリヤカイガラムシ(Icerya purchasi)等のカイガラムシ類、グンバイムシ類、キジラミ類等。 Hemiptera: small brown planthopper (Laodelphax striatellus), brown planthopper (Nilaparvata lugens), Sejirounka (Sogatella furcifera) planthoppers such as, green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens) leafhoppers such as, cotton aphid (Aphis gossypii) , Peaches aphids (Myzus persicae), radish aphids (Brevicorine brassicae), tulip beetle aphids (Macrosiphum euphorbiae), potato aphids (Aulacorthum solani), wheat Aphids such as Rhapalosiphum padi and Toxoptera citricicidus, Nezara tentenis, eus isch, Riptortus clavetus , Larvae (Halyomorpha mista), stink bugs such as tanned plant bug (Lygus lineolaris), Trialureodes vaporiarum, silver leaf whiteflies (Bemisia foliage, etc.) Boiled scale (Aonidiella aurantii), San Jose scaled scale (Comstockcaspis perniciosa), Citrus snow scale (Unaspis citris), Iceria scales, Iceria phylumidum
鱗翅目害虫:ニカメイガ(Chilo suppressalis)、サンカメイガ(Tryporyza incertulas)、コブノメイガ(Cnaphalocrocis medinalis)、ワタノメイガ(Notarcha derogata)、ノシメマダラメイガ(Plodia interpunctella)、アワノメイガ(Ostrinia furnacalis)、ハイマダラノメイガ(Hellula undalis)、シバツトガ(Pediasia teterrellus)等のメイガ類、ハスモンヨトウ(Spodoptera litura)、シロイチモジヨトウ(Spodoptera exigua)、アワヨトウ(Pseudaletia separata)、ヨトウガ(Mamestra brassicae)、タマナヤガ(Agrotis ipsilon)、タマナギンウワバ(Plusia nigrisigna)、トリコプルシア属、ヘリオティス属、ヘリコベルパ属等のヤガ類、モンシロチョウ(Pieris rapae)等のシロチョウ類、アドキソフィエス属、ナシヒメシンクイ(Grapholita molesta)、マメシンクイガ(Leguminivora glycinivorella)、アズキサヤムシガ(Matsumuraeses azukivora)、リンゴコカクモンハマキ(Adoxophyes orana fasciata)、チャノコカクモンハマキ(Adoxophyes sp.)、チャハマキ(Homona magnanima)、ミダレカクモンハマキ(Archips fuscocupreanus)、コドリンガ(Cydia pomonella)等のハマキガ類、チャノホソガ(Caloptilia theivora)、キンモンホソガ(Phyllonorycter ringoneella)のホソガ類、モモシンクイガ(Carposina niponensis)等のシンクイガ類、リオネティア属等のハモグリガ類、リマントリア属、ユープロクティス属等のドクガ類、コナガ(Plutella xylostella)等のスガ類、ワタアカミムシ(Pectinophora gossypiella)ジャガイモガ(Phthorimaea operculella)等のキバガ類、アメリカシロヒトリ(Hyphantria cunea)等のヒトリガ類、イガ(Tinea translucens)、コイガ(Tineola bisselliella)等のヒロズコガ類等。
アザミウマ目害虫:ミカンキイロアザミウマ(Frankliniella occidentalis)、ミナミキイロアザミウマ(Thrips palmi)、チャノキイロアザミウマ(Scirtothrips dorsalis)、ネギアザミウマ(Thrips tabaci)、ヒラズハナアザミウマ(Frankliniella intonsa)、タバコアザミウマ(Frankliniella fusca)などのアザミウマ類等。
双翅目害虫:イエバエ(Musca domestica)、アカイエカ(Culex pipiens pallens)、ウシアブ(Tabanus trigonus)、タマネギバエ(Hylemya antiqua)、タネバエ(Hylemya platura)、シナハマダラカ(Anopheles sinensis)、イネハモグリバエ(Agromyza oryzae)、イネヒメハモグリバエ(Hydrellia griseola)、イネキモグリバエ(Chloropsoryzae)、ウリミバエ(Dacus cucurbitae)、チチュウカイミバエ(Ceratitis capitata)、マメハモグリバエ(Liriomyza trifolii)等。Lepidoptera: rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Japanese medusa such as Shibata toga (Pediasia teterrellus), Spodoptera litura, Spodoptera exigua, Ayuyotoga (Pseudaletia sepata), Atoga assicae), Agrotis ipsilon, Tamanaginawaba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc. Leguminova glycinnivorella), Azusa yamashiga (Matsumuraeses azukivivora), Apple wolfberry (Adoxophyces orana moss) Fusocopreanus, Cydia pomonella, and other species, Euphoria of the genus Cyptolia, Cypridia isp, etc. Species of the genus Curtis, Suga such as Plutella xylostella, Pterophora gossypiella potato moth (Phthorimaea operculella), and the like anslucens), webbing clothes moth (Tineola bisselliella) Hirozukoga such as such.
Thysanoptera: western flower thrips (Frankliniella occidentalis), Minami thrips (Thrips palmi), yellow tea thrips (Scirtothrips dorsalis), green onion thrips (Thrips tabaci), Hirazuhanaazamiuma (Frankliniella intonsa), tobacco thrips (Frankliniella fusca) thrips, such as Etc.
Diptera: Housefly (Musca domestica), Culex (Culex pipiens pallens), gadfly (Tabanus trigonus), onion maggot (Hylemya antiqua), seedcorn maggot (Hylemya platura), Anopheles sinensis (Anopheles sinensis), rice leafminer (Agromyza oryzae), rice Hydrelia griseola, Bluefly flies (Chloropsoryzae), Dwarf fly (Dacus cucurbitae), Ceratitis capitata, B. riparii folii folii.
甲虫目害虫:ニジュウヤホシテントウ(Epilachna vigintioctopunctata)、ウリハムシ(Aulacophora femoralis)、キスジノミハムシ(Phyllotreta striolata)、イネドロオイムシ(Oulema oryzae)、イネゾウムシ(Echinocnemus squameus)、イネミズゾウムシ(Lissorhoptrus oryzophilus)、ワタミゾウムシ(Anthonomus grandis)、アズキゾウムシ(Callosobruchus chinensis)、シバオサゾウムシ(Sphenophorus venatus)、マメコガネ(Popillia japonica)、ドウガネブイブイ(Anomala cuprea)、コーンルートワームの仲間(Diabrotica spp.)、コロラドハムシ(Leptinotarsa decemlineata)、コメツキムシの仲間(Agriotes spp.)、タバコシバンムシ(Lasioderma serricorne)、ヒメマルカツオブシムシ(Anthrenus verbasci)、コクヌストモドキ(Tribolium castaneum)、ヒラタキクイムシ(Lyctus brunneus)、ゴマダラカミキリ(Anoplophora malasiaca)、マツノキクイムシ(Tomicus piniperda)等。
直翅目害虫:トノサマバッタ(Locusta migratoria)、ケラ(Gryllotalpa africana)、コバネイナゴ(Oxya yezoensis)、ハネナガイナゴ(Oxya japonica)等。
膜翅目害虫:カブラハバチ(Athalia rosae)、ハキリアリ(Acromyrmex spp.)、ファイヤーアント(Solenopsis spp.)等。
線虫類:イネシンガレセンチュウ(Aphelenchoides besseyi)、イチゴメセンチュウ(Nothotylenchus acris)、ダイズシストセンチュウ(Heterodera glycines)サツマイモネコブセンチュウ(Meloidogyne incognita)、キタネグサレセンチュウ(Pratylenchus penetrans)、ニセネコブセンチュウ(Nacobbus aberrans)等。
ゴキブリ目害虫:チャバネゴキブリ(Blattella germanica)、クロゴキブリ(Periplaneta fuliginosa)、ワモンゴキブリ(Periplaneta americana)、トビイロゴキブリ(Periplaneta brunnea)、トウヨウゴキブリ(Blatta orientalis)等。
ダニ目害虫:ナミハダニ(Tetranychus urticae)、ミカンハダニ(Panonychus citri)、オリゴニカス属等のハダニ類、ミカンサビダニ(Aculops pelekassi)等のフシダニ類、チャノホコリダニ(Polyphagotarsonemus latus)等のホコリダニ類、ヒメハダニ類、ケナガハダニ類、ケナガコナダニ(Tyrophagus putrescentiae)等のコナダニ類、コナヒョウヒダニ(Dermatophagoides farinae)、ヤケヒョウヒダニ(Dermatophagoides ptrenyssnus)等のヒョウヒダニ類、ホソツメダニ(Cheyletus eruditus)、クワガタツメダニ(Cheyletus malaccensis)、ミナミツメダニ(Cheyletus moorei)等のツメダニ類、ワクモ類等。Coleoptera: beetle, Epilachna vigintioctopunctata (Epilachna vigintioctopunctata), cucurbit leaf beetle (Aulacophora femoralis), Kisujinomihamushi (Phyllotreta striolata), Inedorooimushi (Oulema oryzae), rice weevil (Echinocnemus squameus), rice water weevil (Lissorhoptrus oryzophilus), boll weevil (Anthonomus grandis), Azuki beetle (Callosobruchus chinensis), Shibahorusu weevil (Sphenophorus venatus), Japanese beetle (Popilia japonica), Douganebububu (Anomala cupre) ), Corn rootworm mate (Diabrotica spp.), Colorado potato beetle (Leptinotarsa decemlineata), beetle beetle (Agriotes spp.), Tobacco beetle (Lasiderma serricorne), reverb worm Oyster beetle (Lyctus bruneus), Japanese beetle beetle (Anoprophora malasiaca), pine beetle (Tomicus pinipeda) and the like.
Direct insect pests: Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Oyana japonica, etc.
Hymenoptera: Athalia rosae, Achillyrmex spp., Fire ant (Solenopsis spp.) And the like.
Nematodes: Rice moth nematode (Aphelenchoides besseyy), Strawberry nematode (Heterodera glycines) .
Cockroach pests: German cockroaches (Blatella germanica), Black cockroaches (Periplaneta furiginosa), American cockroaches (Periplaneta americana), Japanese cockroaches (Peripraneta brunet)
Acarina: Tetranychus urticae, Pandychus citri, Odonidus spp., Acarops pelekassi, Mite, Phyphagotaris Mite, such as Typhophagus putrescentiae, Mite, Dermatophagoides falinae, Mite, Mite censis), Tsumedani such as Minami Tsumedani (Cheyletus moorei), chicken mites, and the like.
また、本発明化合物またはその塩を含有する製剤は、家畜病治療の分野および畜産業において、また、脊椎動物、例えば、人間、牛、羊、ヤギ、豚、家禽、犬、猫および魚等の内部および/または外部に寄生する生物や寄生虫を駆除して公衆衛生を維持するのに使用可能である。例えば、該有害生物の中には、マダニ類(Ixodes spp. (例えば、Ixodes scapularis)、ウシマダニ類(Boophilus spp.(例えばオウシマダニ(Boophilus microplus)、キララマダニ類(Amblyomma spp.)、 イボマダニ類(Hyalomma spp.)、コイタマダニ類(Rhipicephalus spp.(例えばクリイロコイタマダニ(Rhipicephalus sanguineus))、チマダニ類(Haemaphysalis spp. .(例えばフタトゲチマダニ(Haemaphysalis longicornis))、 カクマダニ類(dermacentor spp.)、 カズキダニ類(Ornithodoros spp.(例えばOrnithodoros moubata))、ワクモ(Dermahyssus gallinae)、 トリサシダニ(Ornithonyssus sylviarum)、ヒゼンダニ類(Sarcoptes spp.(例えばヒゼンダニ(Sarcoptes scabiei)、 キュウセンヒゼンダニ類(Psoroptes spp.)、ショクヒヒゼンダニ類(Chorioptes spp.)、 ニキビダニ類(Demodex spp.)、ツツガムシ類(Eutrombicula spp.)、ヤブカ類(Aedes spp. 例えばヒトスジシマカ(Aedes albopictus))、ハマダラカ類(Anopheles spp.)、イエカ類(Culex spp)、ヌカカ類(Culicodes spp)、 イエバエ類(Musca spp.)、 ウシバエ類(Hypoderma spp.)、 ウマバエ類(Gasterophilus spp.)、サシバエ類(Haematobia spp)、ウシアブ類(Tabanus spp)、ブユ類(Simulium spp.)、サシガメ類(Triatoma spp.、シラミ類(Phthiraptera(例えばDamalinia spp.、 Linognathus spp.、Haematopinus spp))、ノミ類(Ctenocephalides spp. 例えば、ネコノミ(Ctenocephalides felis)Xenosylla spp)、イエヒメアリ(monomorium pharaonis)および線虫類〔例えば毛様線虫類(例えばNippostrongylus brasiliensis、 Trichostrongylus axei、Trichostrongylus colubriformis)、旋毛虫類(例えばTrichinella spiralis)、捻転胃虫( Haemonchus contortus)、ネマトジルス類(例えば Nematodirus battus)、 オステルターグ胃虫(Ostertagia circumcincta)、クーペリア類 (Cooperia spp.)、矮小条虫(Hymenolepis nana)〕等が挙げられる。 In addition, the preparation containing the compound of the present invention or a salt thereof is used in the field of livestock disease treatment and livestock industry, and in vertebrates such as humans, cows, sheep, goats, pigs, poultry, dogs, cats and fish. It can be used to maintain public health by combating organisms and parasites that parasitize inside and / or outside. For example, the pests include ticks (Ixodes spp. (E.g., Ixodes scapularis), bovine ticks (Boophilus spp. (E.g., Boophilus microplus), larvae ticks (Amblyomma splo. ), Rhipicephalus spp. (Eg, Rhipicephus sanguisus tick (Haemphysalis sp.), (Eg, Haemaphysalis sp. p. (eg, Ornithodoros moubata), duck (Dermahyssus gallinae), ornithonyss sylviarum, mites (Sarcoptes spp.) spp.), Acne mites (Demodex spp.), Tsutsugamushi (Eurombicula spp.), Aedes spp. For example, Aedes albopictus, Anopheles spp. C, Anopheles spp. (Culico des spp), houseflies (Musca spp.), cow flies (Hypoderma spp.), horseflies (Gasterophilus spp.), flies (Haematobia spp), cattle fly (Tabanum spp. Triatoma spp., Lice (Phthiraptera (eg, Damalinia spp., Linognathus spp., Haematopinus spp)), fleas (Ctenocephalides spp. For example) Reptiles (for example, Hair-like nematodes (for example Nippostrongylus brasiliensis, Trichostrongylus axei, Trichostrongylus colubriformis), trichinosis (such Trichinella spiralis), Haemonchus (Haemonchus contortus), Nematojirusu (such Nematodirus battus), Osuterutagu stomach worm (Ostertagia circumcincta), Couperias (Cooperia spp. ), Hymenolepis nana] and the like.
次に本発明について製造例、製剤例、試験例等の実施例によりさらに具体的に説明するが、本発明はこれらの例のみに限定されるものではない。
まず、製造例を示す。
製造例1
C02A 1.10g、参考製造例12記載の1−(4−クロロフェニル)−1H−ピラゾール−3−オール1.01g、炭酸カリウム0.94gおよびN,N−ジメチルホルムアミド15mLの混合物を80℃で3.5時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−tert−ブチル−5−{[1−(4−クロロフェニル)−1H−ピラゾール−3−イル]オキシメチル}−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物1と記す)を1.06g得た。
1H−NMR(CDCl3)δ:7.71(1H,s),7.67(1H,d,J=2.4Hz),7.49(2H,d,J=9.0Hz),7.37(2H,d,J=8.8Hz),5.86(1H,d,J=2.4Hz),5.45(2H,s),3.60(3H,s),1.74(9H,s).Next, the present invention will be described more specifically with reference to Examples such as Production Examples, Formulation Examples, and Test Examples. However, the present invention is not limited to these examples.
First, a manufacturing example is shown.
Production Example 1
A mixture of 1.02 g of C02A, 1.01 g of 1- (4-chlorophenyl) -1H-pyrazol-3-ol described in Reference Production Example 12, 0.94 g of potassium carbonate and 15 mL of N, N-dimethylformamide at 80 ° C. Stir for 5 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (1-tert-butyl-5-{[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxymethyl} -1H-pyrazole- 1.06 g of 4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 1) was obtained.
1 H-NMR (CDCl 3 ) δ: 7.71 (1H, s), 7.67 (1H, d, J = 2.4 Hz), 7.49 (2H, d, J = 9.0 Hz), 7 .37 (2H, d, J = 8.8 Hz), 5.86 (1H, d, J = 2.4 Hz), 5.45 (2H, s), 3.60 (3H, s), 1.74 (9H, s).
製造例2
C02A 0.40g、参考製造例16記載の4−(1−アダマンチル)−2,3−ジヒドロ−2−オキソチアゾール0.30g、炭酸セシウム0.50gおよびN,N−ジメチルホルムアミド15mLの混合物を80℃で0.5時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、2−{[4−(4,5−ジヒドロ−4−メチル−5−オキソ−1H−テトラゾール−1−イル)−2−tert−ブチルピラゾール−3−イル]メチルオキシ}−4−(1−アダマンチル)チアゾール(以下、本発明化合物2と記す)を0.56g得た。
1H−NMR(CDCl3)δ:1.70−1.76(15H,br m),1.84(6H,d,J=2.7Hz),2.03−2.06(3H,m),3.68(3H,s),5.62(2H,s),6.17(1H,s),7.72(1H,s).Production Example 2
A mixture of 0.40 g of C02A, 0.30 g of 4- (1-adamantyl) -2,3-dihydro-2-oxothiazole described in Reference Production Example 16, 0.50 g of cesium carbonate and 15 mL of N, N-dimethylformamide was prepared. Stir at 0 ° C. for 0.5 hour. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2-{[4- (4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl) -2-tert-butylpyrazole- 0.56 g of 3-yl] methyloxy} -4- (1-adamantyl) thiazole (hereinafter referred to as the present compound 2) was obtained.
1 H-NMR (CDCl 3 ) δ: 1.70-1.76 (15H, br m), 1.84 (6H, d, J = 2.7 Hz), 2.03-2.06 (3H, m ), 3.68 (3H, s), 5.62 (2H, s), 6.17 (1H, s), 7.72 (1H, s).
製造例3
C02A 0.11g、参考製造例16記載の4−(4−クロロフェニル)−2,3−ジヒドロ−2−オキソチアゾール0.08g、炭酸セシウム0.13gおよびN,N−ジメチルホルムアミド10mLの混合物を80℃で1時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、2−(4−クロロフェニル)−4−{[4−(4,5−ジヒドロ−4−メチル−5−オキソ−1H−テトラゾール−1−イル)−2−tert−ブチルピラゾール−3−イル]メチルオキシ}チアゾール(以下、本発明化合物3と記す。)を0.08g得た。
1H−NMR(CDCl3)δ:1.75(9H,s),3.56(3H,s),5.73(2H,s),6.86(1H,s),7.35(2H,d,J=8.3Hz),7.68(2H,d,J=8.3Hz),7.73(1H,s).Production Example 3
A mixture of 0.12 g of C02A, 0.08 g of 4- (4-chlorophenyl) -2,3-dihydro-2-oxothiazole described in Reference Production Example 16, 0.13 g of cesium carbonate and 10 mL of N, N-dimethylformamide was added. Stir at 1 ° C. for 1 hour. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (4-chlorophenyl) -4-{[4- (4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl). 0.08 g of 2-tert-butylpyrazol-3-yl] methyloxy} thiazole (hereinafter referred to as the present compound 3) was obtained.
1 H-NMR (CDCl 3 ) δ: 1.75 (9H, s), 3.56 (3H, s), 5.73 (2H, s), 6.86 (1H, s), 7.35 ( 2H, d, J = 8.3 Hz), 7.68 (2H, d, J = 8.3 Hz), 7.73 (1H, s).
製造例4
C02A 0.30g、参考製造例16記載の4−(4−ブロモフェニル)−2,3−ジヒドロ−2−オキソチアゾール0.24g、炭酸セシウム0.37gおよびN,N−ジメチルホルムアミド10mLの混合物を80℃で1時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、2−(4−ブロモフェニル)−4−{[4−(4,5−ジヒドロ−4−メチル−5−オキソ−1H−テトラゾール−1−イル)−2−tert−ブチルピラゾール−3−イル]メチルオキシ}チアゾール(以下、本発明化合物4と記す。)を0.25g得た。
1H−NMR(CDCl3)δ:1.75(9H,s),3.57(3H,s),5.73(2H,s),6.88(1H,s),7.52(2H,d,J=8.5Hz),7.63(2H,d,J=8.5Hz),7.73(1H,s).Production Example 4
A mixture of 0.30 g of C02A, 0.24 g of 4- (4-bromophenyl) -2,3-dihydro-2-oxothiazole described in Reference Production Example 16, 0.37 g of cesium carbonate and 10 mL of N, N-dimethylformamide was prepared. Stir at 80 ° C. for 1 hour. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (4-bromophenyl) -4-{[4- (4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl). ) -2-tert-butylpyrazol-3-yl] methyloxy} thiazole (hereinafter referred to as the present compound 4) was obtained in an amount of 0.25 g.
1 H-NMR (CDCl 3 ) δ: 1.75 (9H, s), 3.57 (3H, s), 5.73 (2H, s), 6.88 (1H, s), 7.52 ( 2H, d, J = 8.5 Hz), 7.63 (2H, d, J = 8.5 Hz), 7.73 (1H, s).
製造例5
C02A 0.30g、参考製造例16記載の4−(4−フルオロフェニル)−2,3−ジヒドロ−2−オキソチアゾール0.19g、炭酸セシウム0.37gおよびN,N−ジメチルホルムアミド10mLの混合物を80℃で1.5時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、2−(4−フルオロフェニル)−4−{[4−(4,5−ジヒドロ−4−メチル−5−オキソ−1H−テトラゾール−1−イル)−2−tert−ブチルピラゾール−3−イル]メチルオキシ}チアゾール(以下、本発明化合物5と記す。)を0.20g得た。
1H−NMR(CDCl3)δ:7.76−7.70(3H,m),7.08(2H,t,J=8.66Hz),6.80(1H,s),5.73(2H,s),3.56(3H,s),1.75(9H,s).Production Example 5
A mixture of 0.30 g of C02A, 0.19 g of 4- (4-fluorophenyl) -2,3-dihydro-2-oxothiazole described in Reference Production Example 16, 0.37 g of cesium carbonate and 10 mL of N, N-dimethylformamide was prepared. The mixture was stirred at 80 ° C. for 1.5 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (4-fluorophenyl) -4-{[4- (4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl). ) -2-tert-butylpyrazol-3-yl] methyloxy} thiazole (hereinafter referred to as the present compound 5) was obtained in an amount of 0.20 g.
1 H-NMR (CDCl 3 ) δ: 7.76-7.70 (3H, m), 7.08 (2H, t, J = 8.66 Hz), 6.80 (1H, s), 5.73 (2H, s), 3.56 (3H, s), 1.75 (9H, s).
製造例6
C05A 0.40g、参考製造例12記載の1−(4−クロロフェニル)−1H−ピラゾール−3−オール0.29g、炭酸カリウム0.41gおよびアセトニトリル10mLの混合物を加熱還流下4時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(2−{[1−(4−クロロフェニル)−1H−ピラゾール−3−イル]オキシメチル}−ピリジン−3−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物6と記す。)を0.56g得た。
1H−NMR(CDCl3)δ:8.77(1H,dd,J=4.9,1.5Hz),7.85(1H,dd,J=8.0,1.5Hz),7.63(1H,d,J=2.7Hz),7.47−7.43(3H,m),7.37−7.33(2H,m),5.86(1H,d,J=2.7Hz),5.55(2H,s),3.66(3H,s).Production Example 6
A mixture of 0.45 g of C05A, 0.29 g of 1- (4-chlorophenyl) -1H-pyrazol-3-ol described in Reference Production Example 12, 0.41 g of potassium carbonate and 10 mL of acetonitrile was stirred with heating under reflux for 4 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (2-{[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxymethyl} -pyridin-3-yl) -4-methyl. 0.56 g of -1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 6) was obtained.
1 H-NMR (CDCl 3 ) δ: 8.77 (1H, dd, J = 4.9, 1.5 Hz), 7.85 (1H, dd, J = 8.0, 1.5 Hz), 7. 63 (1H, d, J = 2.7 Hz), 7.47-7.43 (3H, m), 7.37-7.33 (2H, m), 5.86 (1H, d, J = 2) .7 Hz), 5.55 (2H, s), 3.66 (3H, s).
製造例7
C07A 0.20g、参考製造例12記載の1−(4−クロロフェニル)−1H−ピラゾール−3−オール0.14g、炭酸カリウム0.20gおよびアセトニトリル10mLの混合物を加熱還流下2時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(2−{[1−(4−クロロフェニル)−1H−ピラゾール−3−イル]オキシメチル}−3−チエニル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物7と記す。)を0.17g得た。
1H−NMR(CDCl3)δ:3.68(3H,s),5.57(2H,s),5.91(1H,d,J=2.7Hz),7.30(1H,d,J=5.3Hz),7.42−7.35(3H,m),7.52(2H,dd,J=6.8,2.2Hz),7.68(1H,d,J=2.7Hz).Production Example 7
A mixture of 0.27 g of C07A, 0.14 g of 1- (4-chlorophenyl) -1H-pyrazol-3-ol described in Reference Production Example 12, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred for 2 hours while heating under reflux. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (2-{[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxymethyl} -3-thienyl) -4-methyl-1. , 4-Dihydrotetrazol-5-one (hereinafter referred to as the present compound 7) was obtained in an amount of 0.17 g.
1 H-NMR (CDCl 3 ) δ: 3.68 (3H, s), 5.57 (2H, s), 5.91 (1H, d, J = 2.7 Hz), 7.30 (1H, d , J = 5.3 Hz), 7.42-7.35 (3H, m), 7.52 (2H, dd, J = 6.8, 2.2 Hz), 7.68 (1H, d, J = 2.7 Hz).
製造例8
C07A C07A 0.25g、参考製造例16記載の4−(4−クロロフェニル)−2,3−ジヒドロ−2−オキソチアゾール0.19g、炭酸セシウム0.36gおよびN,N−ジメチルホルムアミド10mLの混合物を80℃で1.5時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、2−(4−クロロフェニル)−4−{[4−(4,5−ジヒドロ−4−メチル−5−オキソ−1H−テトラゾール−1−イル)−3−チエニル]メチルオキシ}チアゾール(以下、本発明化合物8と記す。)を0.17g得た。
1H−NMR(CDCl3)δ:3.68(3H,s),5.81(2H,s),6.87(1H,s),7.34(1H,d,J=5.5Hz),7.36(2H,dd,J=6.6,1.8Hz),7.44(1H,d,J=5.5Hz),7.74(2H,dd,J=6.6,1.8Hz).Production Example 8
C07A A mixture of 0.25 g of C07A, 0.19 g of 4- (4-chlorophenyl) -2,3-dihydro-2-oxothiazole described in Reference Production Example 16, 0.36 g of cesium carbonate and 10 mL of N, N-dimethylformamide The mixture was stirred at 80 ° C. for 1.5 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (4-chlorophenyl) -4-{[4- (4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl). 0.17 g of -3-thienyl] methyloxy} thiazole (hereinafter referred to as the present compound 8) was obtained.
1 H-NMR (CDCl 3 ) δ: 3.68 (3H, s), 5.81 (2H, s), 6.87 (1H, s), 7.34 (1H, d, J = 5.5 Hz) ), 7.36 (2H, dd, J = 6.6, 1.8 Hz), 7.44 (1H, d, J = 5.5 Hz), 7.74 (2H, dd, J = 6.6) 1.8 Hz).
製造例9
C07A 0.20g、参考製造例16記載の4−(4−ブロモフェニル)−2,3−ジヒドロ−2−オキソチアゾール0.19g、炭酸セシウム0.28gおよびN,N−ジメチルホルムアミド10mLの混合物を80℃で1.5時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、2−(4−ブロモフェニル)−4−{[4−(4,5−ジヒドロ−4−メチル−5−オキソ−1H−テトラゾール−1−イル)−3−チエニル]メチルオキシ}チアゾール(以下、本発明化合物9と記す。)を0.05g得た。
1H−NMR(CDCl3)δ:3.65(3H,s),5.18(2H,s),5.97(1H,s),7.03(2H,d,J=8.5Hz),7.12(1H,d,J=5.5Hz),7.29(1H,d,J=5.5Hz),7.46(2H,d,J=8.5Hz).Production Example 9
A mixture of 0.20 g of C07A, 0.19 g of 4- (4-bromophenyl) -2,3-dihydro-2-oxothiazole described in Reference Production Example 16, 0.28 g of cesium carbonate and 10 mL of N, N-dimethylformamide. The mixture was stirred at 80 ° C. for 1.5 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2- (4-bromophenyl) -4-{[4- (4,5-dihydro-4-methyl-5-oxo-1H-tetrazol-1-yl). 0.05 g of) -3-thienyl] methyloxy} thiazole (hereinafter referred to as the present compound 9) was obtained.
1 H-NMR (CDCl 3 ) δ: 3.65 (3H, s), 5.18 (2H, s), 5.97 (1H, s), 7.03 (2H, d, J = 8.5 Hz) ), 7.12 (1H, d, J = 5.5 Hz), 7.29 (1H, d, J = 5.5 Hz), 7.46 (2H, d, J = 8.5 Hz).
製造例10
C09A 0.25g、参考製造例12記載の1−(4−クロロフェニル)−1H−ピラゾール−3−オール0.18g、炭酸カリウム0.15gおよびアセトニトリル10mLの混合物を加熱還流下5時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−メチル−3−{[1−(4−クロロフェニル)−1H−ピラゾール−3−イル]オキシメチル}−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物10と記す。)を0.21g得た。
1H−NMR(CDCl3)δ:7.87(1H,s),7.66(1H,d,J=2.5Hz),7.52(2H,dt,J=9.5,2.6Hz),7.36(2H,dt,J=9.5,2.6Hz),5.91(1H,d,J=2.5Hz),5.46(2H,s),3.97(3H,s),3.62(3H,s).Production Example 10
A mixture of 0.25 g of C09A, 0.18 g of 1- (4-chlorophenyl) -1H-pyrazol-3-ol described in Reference Production Example 12, 0.15 g of potassium carbonate and 10 mL of acetonitrile was stirred with heating under reflux for 5 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 1- (1-methyl-3-{[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxymethyl} -1H-pyrazole-4- Yl) -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 10) 0.21 g was obtained.
1 H-NMR (CDCl 3 ) δ: 7.87 (1H, s), 7.66 (1H, d, J = 2.5 Hz), 7.52 (2H, dt, J = 9.5, 2. 6 Hz), 7.36 (2H, dt, J = 9.5, 2.6 Hz), 5.91 (1H, d, J = 2.5 Hz), 5.46 (2H, s), 3.97 ( 3H, s), 3.62 (3H, s).
製造例11
C11A 0.30g、参考製造例12記載の1−(4−クロロフェニル)−1H−ピラゾール−3−オール0.21g、炭酸カリウム0.18gおよびアセトニトリル10mLの混合物を加熱還流下5時間攪拌した。放冷した反応混合物に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−メチル−5−{[1−(4−クロロフェニル)−1H−ピラゾール−3−イル]オキシメチル}−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物11と記す。)を0.30g得た。
1H−NMR(CDCl3)δ:7.77(1H,s),7.67(1H,d,J=2.5Hz),7.46(2H,dt,J=9.4,2.5Hz),7.37(2H,dt,J=9.5,2.5Hz),5.88(1H,d,J=2.5Hz),5.46(2H,s),4.03(3H,s),3.64(3H,s).Production Example 11
A mixture of 0.31 g of C11A, 0.21 g of 1- (4-chlorophenyl) -1H-pyrazol-3-ol described in Reference Production Example 12, 0.18 g of potassium carbonate and 10 mL of acetonitrile was stirred with heating under reflux for 5 hours. Water was poured into the reaction mixture allowed to cool, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (1-methyl-5-{[1- (4-chlorophenyl) -1H-pyrazol-3-yl] oxymethyl} -1H-pyrazole-4- Yl) -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 11) was obtained in an amount of 0.30 g.
1 H-NMR (CDCl 3 ) δ: 7.77 (1H, s), 7.67 (1H, d, J = 2.5 Hz), 7.46 (2H, dt, J = 9.4, 2. 5 Hz), 7.37 (2H, dt, J = 9.5, 2.5 Hz), 5.88 (1H, d, J = 2.5 Hz), 5.46 (2H, s), 4.03 ( 3H, s), 3.64 (3H, s).
製造例12
C02A 0.50g、参考製造例14に記載の1−(2−メトキシフェニル)−1H−ピラゾール−3−オール0.36g、炭酸カリウム0.26g、アセトニトリル26mLの混合物を60℃で1時間攪拌した。反応混合物に飽和重層水を加え、酢酸エチルで抽出した。有機層を飽和重層水で洗浄し、無水硫酸ナトリウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−tert−ブチル−5−{[1−(2−メトキシフェニル)−1H−ピラゾール−3−イル]オキシメチル}−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物12と記す。)0.17gを得た。
1H−NMR(CDCl3)δ:7.90(1H,d,J=2.1Hz),7.71(1H,s),7.66(1H,dd,J=7.9,1.7Hz),7.23(1H,td,J=7.8,1.7Hz),7.05−7.03(2H,m),5.80(1H,d,J=2.1Hz),5.44(2H,s),3.89(3H,s),3.58(3H,s),1.75(9H,s).Production Example 12
A mixture of 0.50 g of C02A, 0.36 g of 1- (2-methoxyphenyl) -1H-pyrazol-3-ol described in Reference Production Example 14, 0.26 g of potassium carbonate, and 26 mL of acetonitrile was stirred at 60 ° C. for 1 hour. . Saturated multistory water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated multilayer water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (1-tert-butyl-5-{[1- (2-methoxyphenyl) -1H-pyrazol-3-yl] oxymethyl} -1H-pyrazole. 0.17 g of -4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 12) was obtained.
1H-NMR (CDCl3) δ: 7.90 (1H, d, J = 2.1 Hz), 7.71 (1H, s), 7.66 (1H, dd, J = 7.9, 1.7 Hz) , 7.23 (1H, td, J = 7.8, 1.7 Hz), 7.05-7.03 (2H, m), 5.80 (1H, d, J = 2.1 Hz), 5. 44 (2H, s), 3.89 (3H, s), 3.58 (3H, s), 1.75 (9H, s).
製造例13
C11A 0.30g、参考製造例14に記載の1−(2−メトキシフェニル)−1H−ピラゾール−3−オール0.25g、炭酸カリウム0.18g、アセトニトリル18mLの混合物を60℃で1時間攪拌した。反応混合物に飽和重層水を加え、酢酸エチルで抽出した。有機層を飽和重層水で洗浄し、無水硫酸ナトリウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−メチル−5−{[1−(2−メトキシフェニル)−1H−ピラゾール−3−イル]オキシメチル}−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物13と記す。)0.13gを得た。
1H−NMR(CDCl3)δ:7.87(1H,d,J=2.5Hz),7.76(1H,s),7.59(1H,dd,J=7.8,1.7Hz),7.23(1H,ddd,J=8.8,7.0,1.2Hz),7.06−7.00(2H,m),5.81(1H,d,J=2.7Hz),5.45(2H,s),4.03(3H,s),3.88(3H,s),3.61(3H,s).Production Example 13
A mixture of 0.31 g of C11A, 0.25 g of 1- (2-methoxyphenyl) -1H-pyrazol-3-ol described in Reference Production Example 14, 0.18 g of potassium carbonate, and 18 mL of acetonitrile was stirred at 60 ° C. for 1 hour. . Saturated multistory water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated multilayer water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (1-methyl-5-{[1- (2-methoxyphenyl) -1H-pyrazol-3-yl] oxymethyl} -1H-pyrazole-4. -Il) -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 13) 0.13 g was obtained.
1H-NMR (CDCl3) δ: 7.87 (1H, d, J = 2.5 Hz), 7.76 (1H, s), 7.59 (1H, dd, J = 7.8, 1.7 Hz) , 7.23 (1H, ddd, J = 8.8, 7.0, 1.2 Hz), 7.06-7.00 (2H, m), 5.81 (1H, d, J = 2.7 Hz) ), 5.45 (2H, s), 4.03 (3H, s), 3.88 (3H, s), 3.61 (3H, s).
製造例14
C02A 0.50g、参考製造例21記載の4−(5−クロロ−1,4−ジメチル−1H−ピラゾール−3−イル)−2−メチル−フェノール0.38g、炭酸カリウム0.26g、N,N−ジメチルホルムアミド26mLの混合物を60℃で1時間攪拌した。反応混合物に飽和重層水を加え、酢酸エチルで抽出した。有機層を飽和重層水で洗浄し、無水硫酸ナトリウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−tert−ブチル−5−[2−メチル−4−(5−クロロ−1,4−ジメチル−1H−ピラゾール−3−イル)−フェノキシメチル]−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物14と記す。)0.25gを得た。
1H−NMR(CDCl3)δ:7.74(1H,s),7.44(1H,s),7.39(1H,d,J=8.2Hz),6.88(1H,d,J=8.5Hz),5.16(2H,s),3.86(3H,s),3.65(3H,s),2.18(3H,s),2.15(3H,s),1.74(9H,s).Production Example 14
C02A 0.50 g, 4- (5-chloro-1,4-dimethyl-1H-pyrazol-3-yl) -2-methyl-phenol 0.38 g described in Reference Production Example 21, potassium carbonate 0.26 g, N, A mixture of 26 mL of N-dimethylformamide was stirred at 60 ° C. for 1 hour. Saturated multistory water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated multilayer water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (1-tert-butyl-5- [2-methyl-4- (5-chloro-1,4-dimethyl-1H-pyrazol-3-yl). -Phenoxymethyl] -1H-pyrazol-4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 14) 0.25 g was obtained.
1H-NMR (CDCl3) δ: 7.74 (1H, s), 7.44 (1H, s), 7.39 (1H, d, J = 8.2 Hz), 6.88 (1H, d, J = 8.5 Hz), 5.16 (2H, s), 3.86 (3H, s), 3.65 (3H, s), 2.18 (3H, s), 2.15 (3H, s) , 1.74 (9H, s).
製造例15
C11A 0.30g、参考製造例22に記載の4−(5−クロロ−1,4−ジメチル−1H−ピラゾール−3−イル)−2−メチル−フェノール0.26g、炭酸カリウム0.18g、N,N−ジメチルホルムアミド18mLの混合物を60℃で1時間攪拌した。反応混合物に飽和重層水を加え、酢酸エチルで抽出した。有機層を飽和重層水で洗浄し、無水硫酸ナトリウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−メチル−5−[2−メチル−4−(5−クロロ−1,4−ジメチル−1H−ピラゾール−3−イル)−フェノキシメチル]−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物15と記す。)0.39gを得た。
1H−NMR(CDCl3)δ:7.80(1H,s),7.45(1H,s),7.40(1H,dd,J=8.5,2.1Hz),6.92(1H,d,J=8.5Hz),5.20(2H,s),4.02(3H,s),3.86(3H,s),3.69(3H,s),2.21(3H,s),2.15(3H,s).Production Example 15
0.31 g of C11A, 0.26 g of 4- (5-chloro-1,4-dimethyl-1H-pyrazol-3-yl) -2-methyl-phenol described in Reference Production Example 22, 0.18 g of potassium carbonate, N , N-dimethylformamide 18 mL was stirred at 60 ° C. for 1 hour. Saturated multistory water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated multilayer water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (1-methyl-5- [2-methyl-4- (5-chloro-1,4-dimethyl-1H-pyrazol-3-yl) -phenoxy. 0.39 g of methyl] -1H-pyrazol-4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 15) was obtained.
1H-NMR (CDCl3) δ: 7.80 (1H, s), 7.45 (1H, s), 7.40 (1H, dd, J = 8.5, 2.1 Hz), 6.92 (1H , D, J = 8.5 Hz), 5.20 (2H, s), 4.02 (3H, s), 3.86 (3H, s), 3.69 (3H, s), 2.21 ( 3H, s), 2.15 (3H, s).
製造例16
C05A 0.47g、参考製造例22に記載の4−(5−クロロ−1,4−ジメチル−1H−ピラゾール−3−イル)−2−メチル−フェノール0.41g、炭酸カリウム0.29g、N,N−ジメチルホルムアミド28mLの混合物を60℃で1時間攪拌した。反応混合物に飽和重層水を加え、酢酸エチルで抽出した。有機層を飽和重層水で洗浄し、無水硫酸ナトリウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(2−[2−メチル−4−(5−クロロ−1,4−ジメチル−1H−ピラゾール−3−イル)−フェノキシメチル]−ピリジン−3−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(以下、本発明化合物16と記す。)0.25gを得た。
1H−NMR(CDCl3)δ:8.75(1H,dd,J=4.8,1.6Hz),7.87(1H,dd,J=8.0,1.6Hz),7.49(1H,dd,J=8.0,4.8Hz),7.38(1H,d,J=1.4Hz),7.33(1H,dd,J=8.5,1.8Hz),6.88(1H,d,J=8.5Hz),5.46(2H,s),3.84(3H,s),3.62(3H,s),2.13(3H,s),2.02(3H,s).Production Example 16
0.45 g of C05A, 0.41 g of 4- (5-chloro-1,4-dimethyl-1H-pyrazol-3-yl) -2-methyl-phenol described in Reference Production Example 22, 0.29 g of potassium carbonate, N , N-dimethylformamide 28 mL was stirred at 60 ° C. for 1 hour. Saturated multistory water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated multilayer water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (2- [2-methyl-4- (5-chloro-1,4-dimethyl-1H-pyrazol-3-yl) -phenoxymethyl] -pyridine. -3-g) -4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 16) 0.25 g was obtained.
1H-NMR (CDCl3) δ: 8.75 (1H, dd, J = 4.8, 1.6 Hz), 7.87 (1H, dd, J = 8.0, 1.6 Hz), 7.49 ( 1H, dd, J = 8.0, 4.8 Hz), 7.38 (1H, d, J = 1.4 Hz), 7.33 (1H, dd, J = 8.5, 1.8 Hz), 6 .88 (1H, d, J = 8.5 Hz), 5.46 (2H, s), 3.84 (3H, s), 3.62 (3H, s), 2.13 (3H, s), 2.02 (3H, s).
参考製造例1
1−tert−ブチル−5−メチル−1H−ピラゾール−4−カルボン酸9.50g、二塩化オキサリル7.28g、N,N−ジメチルホルムアミド約75mgおよびテトラヒドロフラン200mLの混合物を25℃で1時間攪拌した。反応混合物を減圧下濃縮し、1−tert−ブチル−5−メチル−1H−ピラゾール−4−カルボン酸クロリドを得た。
塩化アルミニウム13.90g、アジ化ナトリウム20.34gおよびテトラヒドロフラン100mLの混合物を加熱還流下2時間攪拌した。反応混合物を氷冷後、1−tert−ブチル−5−メチル−1H−ピラゾール−4−カルボン酸クロリドおよびテトラヒドロフラン100mLの混合物を反応混合物に加え、加熱還流下3日間攪拌した。冷却後、反応混合物を亜硝酸ナトリウム31.29gおよび水100mLの混合物中に攪拌しながら加えた。混合物を濃塩酸で酸性とした後、酢酸エチルで抽出した。有機層を無水硫酸ナトリウムで乾燥した後、減圧下に濃縮後、1−(1−tert−ブチル−5−メチル−1H−ピラゾール−4−イル)−1,4−ジヒドロテトラゾール−5−オン13.40gを得た。
1−(1−tert−ブチル−5−メチル−1H−ピラゾール−4−イル)−1,4−ジヒドロテトラゾール−5−オン、炭酸カリウム23.78g、ジメチル硫酸7.89gおよびN,N−ジメチルホルムアミド100mLの混合物を25℃で1時間攪拌した。反応混合物に飽和重曹水を注加し、酢酸エチルで抽出した。有機層を飽和重曹水で洗浄し、無水硫酸ナトリウムで乾燥した。減圧下に濃縮し、1−(1−tert−ブチル−5−メチル−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C01Aと記す)8.85gを得た。
1H−NMR(CDCl3)δ:7.58(1H,s),3.70(3H,s),2.40(3H,s),1.68(9H,s).Reference production example 1
A mixture of 9.50 g of 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylic acid, 7.28 g of oxalyl dichloride, about 75 mg of N, N-dimethylformamide and 200 mL of tetrahydrofuran was stirred at 25 ° C. for 1 hour. . The reaction mixture was concentrated under reduced pressure to obtain 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylic acid chloride.
A mixture of 13.90 g of aluminum chloride, 20.34 g of sodium azide and 100 mL of tetrahydrofuran was stirred with heating under reflux for 2 hours. After the reaction mixture was ice-cooled, a mixture of 1-tert-butyl-5-methyl-1H-pyrazole-4-carboxylic acid chloride and 100 mL of tetrahydrofuran was added to the reaction mixture, and the mixture was stirred for 3 days with heating under reflux. After cooling, the reaction mixture was added to a mixture of 31.29 g sodium nitrite and 100 mL water with stirring. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and then 1- (1-tert-butyl-5-methyl-1H-pyrazol-4-yl) -1,4-dihydrotetrazol-5-one 13 .40 g was obtained.
1- (1-tert-butyl-5-methyl-1H-pyrazol-4-yl) -1,4-dihydrotetrazol-5-one, potassium carbonate 23.78 g, dimethyl sulfate 7.89 g and N, N-dimethyl A mixture of 100 mL formamide was stirred at 25 ° C. for 1 hour. Saturated aqueous sodium hydrogen carbonate was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate. Concentration under reduced pressure gave 8.85 g of 1- (1-tert-butyl-5-methyl-1H-pyrazol-4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (denoted as C01A). Got.
1 H-NMR (CDCl 3 ) δ: 7.58 (1H, s), 3.70 (3H, s), 2.40 (3H, s), 1.68 (9H, s).
参考製造例2
C01A 1.00g、1,1’−アゾビス(シクロヘキサン−1−カルボニトリル)0.41g、N−ブロモスクシンイミド0.87gおよびクロロベンゼン30mLの混合物を加熱還流下3時間攪拌した。冷却後、反応液に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−tert−ブチル−5−ブロモメチル−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C02Aと記す)1.10gを得た。
1H−NMR(CDCl3)δ:7.73(1H,s),4.81(2H,s),3.72(3H,s),1.75(9H,s).Reference production example 2
A mixture of 1.00 g of C01A, 0.41 g of 1,1′-azobis (cyclohexane-1-carbonitrile), 0.87 g of N-bromosuccinimide and 30 mL of chlorobenzene was stirred with heating under reflux for 3 hours. After cooling, water was poured into the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (1-tert-butyl-5-bromomethyl-1H-pyrazol-4-yl) -4-methyl-1,4-dihydrotetrazol-5-one ( 1.10 g was obtained.
1 H-NMR (CDCl 3 ) δ: 7.73 (1H, s), 4.81 (2H, s), 3.72 (3H, s), 1.75 (9H, s).
参考製造例3
2−メチルピリジン−3−カルボン酸5.00g、二塩化オキサリル3.42g、N,N−ジメチルホルムアミド約75mgおよびテトラヒドロフラン200mLの混合物を25℃で1時間攪拌した。反応混合物を減圧下濃縮し、2−メチルピリジン−3−カルボン酸クロリドを得た。
塩化アルミニウム6.53g、アジ化ナトリウム9.55gおよびテトラヒドロフラン100mLの混合物を加熱還流下2時間攪拌した。反応混合物を氷冷後、2−メチルピリジン−3−カルボン酸クロリドおよびテトラヒドロフラン100mLの混合物を反応混合物に加え、加熱還流下2日間攪拌した。冷却後、反応混合物を亜硝酸ナトリウム14.07gおよび水100mLの混合物中に攪拌しながら加えた。混合物を濃塩酸で酸性とした後、酢酸エチルで抽出した。有機層を無水硫酸ナトリウムで乾燥した後、減圧下に濃縮後、1−(2−メチルピリジン−3−イル)−1,4−ジヒドロテトラゾール−5−オン(C03Aと記す)3.00gを得た。
1H−NMR(DMSO−D6)δ:8.65(1H,dd,J=4.8,1.4Hz),7.95(1H,dd,J=8.0,1.7Hz),7.50(1H,dd,J=8.0,4.8Hz),2.44(3H,s).Reference production example 3
A mixture of 5.00 g of 2-methylpyridine-3-carboxylic acid, 3.42 g of oxalyl dichloride, about 75 mg of N, N-dimethylformamide and 200 mL of tetrahydrofuran was stirred at 25 ° C. for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain 2-methylpyridine-3-carboxylic acid chloride.
A mixture of 6.53 g of aluminum chloride, 9.55 g of sodium azide and 100 mL of tetrahydrofuran was stirred with heating under reflux for 2 hours. After the reaction mixture was ice-cooled, a mixture of 2-methylpyridine-3-carboxylic acid chloride and 100 mL of tetrahydrofuran was added to the reaction mixture, and the mixture was stirred for 2 days with heating under reflux. After cooling, the reaction mixture was added with stirring to a mixture of sodium nitrite 14.07 g and water 100 mL. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 3.00 g of 1- (2-methylpyridin-3-yl) -1,4-dihydrotetrazol-5-one (denoted as C03A). It was.
1 H-NMR (DMSO-D 6 ) δ: 8.65 (1H, dd, J = 4.8, 1.4 Hz), 7.95 (1H, dd, J = 8.0, 1.7 Hz), 7.50 (1H, dd, J = 8.0, 4.8 Hz), 2.44 (3H, s).
参考製造例4
C03A 0.50g、炭酸カリウム1.29g、ジメチル硫酸0.43gおよびN,N−ジメチルホルムアミド15mLの混合物を25℃で1時間攪拌した。反応混合物に飽和重曹水を注加し、酢酸エチルで抽出した。有機層を飽和重曹水で洗浄し、無水硫酸ナトリウムで乾燥した。減圧下に濃縮後、シリカゲルカラムクロマトグラフィーに付し、1−(2−メチルピリジン−3−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C04Aと記す)0.27gを得た。
1H−NMR(CDCl3)δ:8.64(1H,dd,J=4.9,1.6Hz),7.71(1H,dd,J=8.0,1.6Hz),7.32(1H,dd,J=8.0,4.9Hz),3.74(3H,s),2.56(3H,s).Reference production example 4
A mixture of 0.50 g of C03A, 1.29 g of potassium carbonate, 0.43 g of dimethyl sulfate and 15 mL of N, N-dimethylformamide was stirred at 25 ° C. for 1 hour. Saturated aqueous sodium hydrogen carbonate was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to give 0.27 g of 1- (2-methylpyridin-3-yl) -4-methyl-1,4-dihydrotetrazol-5-one (denoted as C04A). Obtained.
1 H-NMR (CDCl 3 ) δ: 8.64 (1H, dd, J = 4.9, 1.6 Hz), 7.71 (1H, dd, J = 8.0, 1.6 Hz), 7. 32 (1H, dd, J = 8.0, 4.9 Hz), 3.74 (3H, s), 2.56 (3H, s).
参考製造例5
C04A 1.00g、1,1’−アゾビス(シクロヘキサン−1−カルボニトリル)0.51g、N−ブロモスクシンイミド1.07gおよびクロロベンゼン10mLの混合物を加熱還流下5時間攪拌した。冷却後、反応液に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(2−ブロモメチル−ピリジン−3−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C05Aと記す)0.23gを得た。
1H−NMR(CDCl3)δ:8.69(1H,dd,J=4.8,1.5Hz),7.85(1H,dd,J=8.1,1.5Hz),7.46(1H,dd,J=8.1,4.8Hz),4.75(2H,s),3.76(3H,s).Reference production example 5
A mixture of 1.00 g of C04A, 0.51 g of 1,1′-azobis (cyclohexane-1-carbonitrile), 1.07 g of N-bromosuccinimide and 10 mL of chlorobenzene was stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.23 g of 1- (2-bromomethyl-pyridin-3-yl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as C05A). Obtained.
1 H-NMR (CDCl 3 ) δ: 8.69 (1H, dd, J = 4.8, 1.5 Hz), 7.85 (1H, dd, J = 8.1, 1.5 Hz), 7. 46 (1H, dd, J = 8.1, 4.8 Hz), 4.75 (2H, s), 3.76 (3H, s).
参考製造例6
2−メチル−3−チエニルカルボン酸3.70g、二塩化オキサリル3.63g、N,N−ジメチルホルムアミド約15mgおよびテトラヒドロフラン50mLの混合物を25℃で1時間攪拌した。反応混合物を減圧下濃縮し、2−メチル−3−チエニルカルボン酸クロリドを得た。
塩化アルミニウム10.15g、アジ化ナトリウム4.18gおよびテトラヒドロフラン20mLの混合物を加熱還流下2時間攪拌した。反応混合物を氷冷後、2−メチル−3−チエニルカルボン酸クロリドおよびテトラヒドロフラン20mLの混合物を反応混合物に加え、加熱還流下10時間攪拌した。冷却後、反応混合物を亜硝酸ナトリウム15.62gおよび水20mLの混合物中に攪拌しながら加えた。混合物を濃塩酸で酸性とした後、酢酸エチルで抽出した。有機層を無水硫酸ナトリウムで乾燥した後、減圧下に濃縮後、1−(2−メチル−3−チエニル)−1,4−ジヒドロテトラゾール−5−オンを得た。
1−(2−メチル−3−チエニル)−1,4−ジヒドロテトラゾール−5−オンの全量、炭酸カリウム11.87g、ジメチル硫酸3.94gおよびN,N−ジメチルホルムアミド20mLの混合物を25℃で1時間攪拌した。反応混合物に飽和重曹水を注加し、酢酸エチルで抽出した。有機層を飽和重曹水で洗浄し、無水硫酸ナトリウムで乾燥した。減圧下に濃縮後、残渣をシリカゲルカラムクロマトグラフィーに付すことで1−(2−メチル−3−チエニル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C06Aと記す)2.64gを得た。
1H−NMR(CDCl3)δ:2.47(3H,s),3.71(3H,s),7.13(1H,d,J=5.5Hz),7.17(1H,d,J=5.5Hz).Reference production example 6
A mixture of 3.70 g of 2-methyl-3-thienylcarboxylic acid, 3.63 g of oxalyl dichloride, about 15 mg of N, N-dimethylformamide and 50 mL of tetrahydrofuran was stirred at 25 ° C. for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain 2-methyl-3-thienylcarboxylic acid chloride.
A mixture of 10.15 g of aluminum chloride, 4.18 g of sodium azide and 20 mL of tetrahydrofuran was stirred with heating under reflux for 2 hours. After cooling the reaction mixture with ice, a mixture of 2-methyl-3-thienylcarboxylic acid chloride and 20 mL of tetrahydrofuran was added to the reaction mixture, and the mixture was stirred for 10 hours under heating to reflux. After cooling, the reaction mixture was added to a mixture of 15.62 g sodium nitrite and 20 mL water with stirring. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 1- (2-methyl-3-thienyl) -1,4-dihydrotetrazol-5-one.
A mixture of the total amount of 1- (2-methyl-3-thienyl) -1,4-dihydrotetrazol-5-one, 11.87 g of potassium carbonate, 3.94 g of dimethyl sulfate and 20 mL of N, N-dimethylformamide at 25 ° C. Stir for 1 hour. Saturated aqueous sodium hydrogen carbonate was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to obtain 2.64 g of 1- (2-methyl-3-thienyl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as C06A). Got.
1 H-NMR (CDCl 3 ) δ: 2.47 (3H, s), 3.71 (3H, s), 7.13 (1H, d, J = 5.5 Hz), 7.17 (1H, d , J = 5.5 Hz).
参考製造例7
C06A 0.30g、1,1’−アゾビス(シクロヘキサン−1−カルボニトリル)0.15g、N−ブロモスクシンイミド0.31gおよびクロロベンゼン5mLの混合物を加熱還流下5時間攪拌した。冷却後、反応液に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(2−ブロモメチル−3−チエニル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C07Aと記す)0.23gを得た。
1H−NMR(CDCl3)δ:3.72(3H,s),4.86(2H,s),7.32(1H,d,J=5.6Hz),7.40(1H,d,J=5.6Hz).Reference production example 7
A mixture of 0.36 g of C06A, 0.15 g of 1,1′-azobis (cyclohexane-1-carbonitrile), 0.31 g of N-bromosuccinimide and 5 mL of chlorobenzene was stirred with heating under reflux for 5 hours. After cooling, water was poured into the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.23 g of 1- (2-bromomethyl-3-thienyl) -4-methyl-1,4-dihydrotetrazol-5-one (denoted as C07A). .
1 H-NMR (CDCl 3 ) δ: 3.72 (3H, s), 4.86 (2H, s), 7.32 (1H, d, J = 5.6 Hz), 7.40 (1H, d , J = 5.6 Hz).
参考製造例8
1,3−ジメチル−1H−ピラゾール−4−カルボン酸1.30g、二塩化オキサリル1.00g、N,N−ジメチルホルムアミド約15mgおよびテトラヒドロフラン50mLの混合物を25℃で1時間攪拌した。反応混合物を減圧下濃縮し、1,3−ジメチル−1H−ピラゾール−4−カルボン酸クロリドを得た。
塩化アルミニウム1.90g、アジ化ナトリウム2.78gおよびテトラヒドロフラン50mLの混合物を加熱還流下2時間攪拌した。反応混合物を氷冷後、1,3−ジメチル−1H−ピラゾール−4−カルボン酸クロリドおよびテトラヒドロフラン50mLの混合物を加え、加熱還流下3日間攪拌した。冷却後、反応混合物を亜硝酸ナトリウム4.28gおよび水100mLの混合物中に攪拌しながら加えた。混合物を濃塩酸で酸性とした後、酢酸エチルで抽出した。有機層を無水硫酸ナトリウムで乾燥した後、減圧下に濃縮後、1−(1,3−ジメチル−1H−ピラゾール−4−イル)−1,4−ジヒドロテトラゾール−5−オン0.7gを得た。
1H−NMR(DMSO−D6)δ:8.07(1H,s),3.82(3H,s),2.13(3H,s).
1−(1,3−ジメチル−1H−ピラゾール−4−イル)−1,4−ジヒドロテトラゾール−5−オン、炭酸カリウム3.25g、ジメチル硫酸1.08gおよびN,N−ジメチルホルムアミド100mLの混合物を60℃で1時間攪拌した。反応混合物に飽和重曹水を注加し、酢酸エチルで抽出した。有機層を飽和重曹水で洗浄し、無水硫酸ナトリウムで乾燥した。減圧下に濃縮後し、1−(1,3−ジメチル−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C08Aと記す)0.50gを得た。
1H−NMR(CDCl3)δ:7.73(1H,s),3.88(3H,s),3.70(3H,s),2.33(3H,s).Reference production example 8
A mixture of 1.30 g of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid, 1.00 g of oxalyl dichloride, about 15 mg of N, N-dimethylformamide and 50 mL of tetrahydrofuran was stirred at 25 ° C. for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain 1,3-dimethyl-1H-pyrazole-4-carboxylic acid chloride.
A mixture of 1.90 g of aluminum chloride, 2.78 g of sodium azide and 50 mL of tetrahydrofuran was stirred with heating under reflux for 2 hours. The reaction mixture was ice-cooled, a mixture of 1,3-dimethyl-1H-pyrazole-4-carboxylic acid chloride and tetrahydrofuran (50 mL) was added, and the mixture was stirred with heating under reflux for 3 days. After cooling, the reaction mixture was added to a mixture of 4.28 g sodium nitrite and 100 mL water with stirring. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 0.7 g of 1- (1,3-dimethyl-1H-pyrazol-4-yl) -1,4-dihydrotetrazol-5-one. It was.
1 H-NMR (DMSO-D 6 ) δ: 8.07 (1H, s), 3.82 (3H, s), 2.13 (3H, s).
Mixture of 1- (1,3-dimethyl-1H-pyrazol-4-yl) -1,4-dihydrotetrazol-5-one, 3.25 g of potassium carbonate, 1.08 g of dimethyl sulfate and 100 mL of N, N-dimethylformamide Was stirred at 60 ° C. for 1 hour. Saturated aqueous sodium hydrogen carbonate was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 0.50 g of 1- (1,3-dimethyl-1H-pyrazol-4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (denoted as C08A) was obtained. .
1 H-NMR (CDCl 3 ) δ: 7.73 (1H, s), 3.88 (3H, s), 3.70 (3H, s), 2.33 (3H, s).
参考製造例9
C08A 0.50g、1,1’−アゾビス(シクロヘキサン−1−カルボニトリル)0.25g、N−ブロモスクシンイミド0.53gおよびクロロベンゼン30mLの混合物を加熱還流下3時間攪拌した。冷却後、反応液に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−メチル−3−ブロモメチル−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C09Aと記す)0.25gを得た。
1H−NMR(CDCl3)δ:7.89(1H,s),4.69(2H,s),3.94(3H,s),3.72(3H,s).Reference production example 9
A mixture of 0.58 g of C08A, 0.25 g of 1,1′-azobis (cyclohexane-1-carbonitrile), 0.53 g of N-bromosuccinimide and 30 mL of chlorobenzene was stirred with heating under reflux for 3 hours. After cooling, water was poured into the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography, and 1- (1-methyl-3-bromomethyl-1H-pyrazol-4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (C09A and 0.25 g was obtained.
1 H-NMR (CDCl 3 ) δ: 7.89 (1H, s), 4.69 (2H, s), 3.94 (3H, s), 3.72 (3H, s).
参考製造例10
1,5−ジメチル−1H−ピラゾール−4−カルボン酸1.60g、二塩化オキサリル1.23g、N,N−ジメチルホルムアミド約15mgおよびテトラヒドロフラン50mLの混合物を25℃で1時間攪拌した。反応混合物を減圧下濃縮し、1,5−ジメチル−1H−ピラゾール−4−カルボン酸クロリドを得た。
塩化アルミニウム2.34g、アジ化ナトリウム3.42gおよびテトラヒドロフラン50mLの混合物を加熱還流下2時間攪拌した。反応混合物を氷冷後、1,5−ジメチル−1H−ピラゾール−4−カルボン酸クロリドおよびテトラヒドロフラン50mLの混合物を反応混合物に加え、加熱還流下3日間攪拌した。冷却後、反応混合物を亜硝酸ナトリウム5.27gおよび水100mLの混合物中に攪拌しながら加えた。混合物を濃塩酸で酸性とした後、酢酸エチルで抽出した。有機層を無水硫酸ナトリウムで乾燥した後、減圧下に濃縮後、1−(1,5−ジメチル−1H−ピラゾール−4−イル)−1,4−ジヒドロテトラゾール−5−オン1.6gを得た。
1H−NMR(DMSO−D6)δ:7.62(1H,s),3.80(3H,s),2.22(3H,s).
1−(1,5−ジメチル−1H−ピラゾール−4−イル)−1,4−ジヒドロテトラゾール−5−オン、炭酸カリウム4.00g、ジメチル硫酸1.33gおよびN,N−ジメチルホルムアミド100mLの混合物を60℃で1時間攪拌した。反応混合物に飽和重曹水を注加し、酢酸エチルで抽出した。有機層を飽和重曹水で洗浄し、無水硫酸ナトリウムで乾燥した。減圧下に濃縮後し、1−(1,5−ジメチル−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C10Aと記す)1.40gを得た。
1H−NMR(CDCl3)δ:7.65(1H,s),3.84(3H,s),3.70(3H,s),2.31(3H,s).Reference production example 10
A mixture of 1.60 g of 1,5-dimethyl-1H-pyrazole-4-carboxylic acid, 1.23 g of oxalyl dichloride, about 15 mg of N, N-dimethylformamide and 50 mL of tetrahydrofuran was stirred at 25 ° C. for 1 hour. The reaction mixture was concentrated under reduced pressure to obtain 1,5-dimethyl-1H-pyrazole-4-carboxylic acid chloride.
A mixture of aluminum chloride (2.34 g), sodium azide (3.42 g) and tetrahydrofuran (50 mL) was stirred with heating under reflux for 2 hours. The reaction mixture was ice-cooled, a mixture of 1,5-dimethyl-1H-pyrazole-4-carboxylic acid chloride and 50 mL of tetrahydrofuran was added to the reaction mixture, and the mixture was stirred for 3 days with heating under reflux. After cooling, the reaction mixture was added to a mixture of sodium nitrite 5.27 g and water 100 mL with stirring. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 1.6 g of 1- (1,5-dimethyl-1H-pyrazol-4-yl) -1,4-dihydrotetrazol-5-one. It was.
1 H-NMR (DMSO-D 6 ) δ: 7.62 (1H, s), 3.80 (3H, s), 2.22 (3H, s).
A mixture of 1- (1,5-dimethyl-1H-pyrazol-4-yl) -1,4-dihydrotetrazol-5-one, 4.00 g of potassium carbonate, 1.33 g of dimethyl sulfate and 100 mL of N, N-dimethylformamide. Was stirred at 60 ° C. for 1 hour. Saturated aqueous sodium hydrogen carbonate was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 1.40 g of 1- (1,5-dimethyl-1H-pyrazol-4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (referred to as C10A) was obtained. .
1 H-NMR (CDCl 3 ) δ: 7.65 (1H, s), 3.84 (3H, s), 3.70 (3H, s), 2.31 (3H, s).
参考製造例11
C10A 1.40g、1,1’−アゾビス(シクロヘキサン−1−カルボニトリル)0.71g、N−ブロモスクシンイミド1.48gおよびクロロベンゼン90mLの混合物を加熱還流下3時間攪拌した。冷却後、反応液に水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付し、1−(1−メチル−5−ブロモメチル−1H−ピラゾール−4−イル)−4−メチル−1,4−ジヒドロテトラゾール−5−オン(C11Aと記す)1.20gを得た。
1H−NMR(CDCl3)δ:7.81(1H,s),4.66(2H,s),3.97(3H,s),3.71(3H,s).Reference production example 11
A mixture of 1.40 g of C10A, 0.71 g of 1,1′-azobis (cyclohexane-1-carbonitrile), 1.48 g of N-bromosuccinimide and 90 mL of chlorobenzene was stirred with heating under reflux for 3 hours. After cooling, water was poured into the reaction solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 1- (1-methyl-5-bromomethyl-1H-pyrazol-4-yl) -4-methyl-1,4-dihydrotetrazol-5-one (with C11A). 1.20 g was obtained.
1 H-NMR (CDCl 3 ) δ: 7.81 (1H, s), 4.66 (2H, s), 3.97 (3H, s), 3.71 (3H, s).
参考製造例12
4−クロロフェニルヒドラジン28.5g、28%ナトリウムメトキシド−メタノール溶液81.3gおよびメタノール200mLの混合物に氷冷下、プロピオール酸メチル29.4gを加え、100℃で2時間攪拌した。放冷した反応混合物に氷水100mLを加え、30%硫酸で酸性とした後、100℃で2時間攪拌した。放冷した反応混合物に飽和食塩水を注加し、酢酸エチルで抽出した。有機層を水および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮し、1−(4−クロロフェニル)−1H−ピラゾール−3−オール15.6gを得た。
1−(4−クロロフェニル)−1H−ピラゾール−3−オール
1H−NMR(DMSO−d6)δ(ppm):5.84(1H,d,J=2.4Hz),7.48(2H,d,J=8.9Hz),7.70(2H,d,J=8.9Hz),8.25(1H,d,J=2.7Hz),10.32(1H,s).Reference production example 12
To a mixture of 28.5 g of 4-chlorophenylhydrazine, 81.3 g of 28% sodium methoxide-methanol solution and 200 mL of methanol, 29.4 g of methyl propiolate was added under ice cooling, and the mixture was stirred at 100 ° C. for 2 hours. To the reaction mixture allowed to cool, 100 mL of ice water was added, acidified with 30% sulfuric acid, and then stirred at 100 ° C. for 2 hours. To the reaction mixture allowed to cool, saturated brine was poured, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give 15.6 g of 1- (4-chlorophenyl) -1H-pyrazol-3-ol.
1- (4-Chlorophenyl) -1H-pyrazol-3-ol
1 H-NMR (DMSO-d 6 ) δ (ppm): 5.84 (1H, d, J = 2.4 Hz), 7.48 (2H, d, J = 8.9 Hz), 7.70 (2H , D, J = 8.9 Hz), 8.25 (1H, d, J = 2.7 Hz), 10.32 (1H, s).
参考製造例13
N−ヒドロキシコハク酸イミド200g、参考製造例30に記載の3−メトキシアクリル酸ナトリウム287g、1−エチル−3−(3−ジメチルアミノプロピル)カルボジイミド塩酸塩528g、ピリジン269gおよびN,N−ジメチルホルムアミド2Lの混合物を室温で44時間攪拌した。反応混合物を重曹水に加えた後、酢酸エチルで抽出した。有機層を飽和重曹水、硫酸水素ナトリウム水溶液および飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下に濃縮した。得られた残渣をtert−ブチルメチルエーテルとヘキサンの混合溶媒で洗浄した後、減圧下に乾燥し、スクシンイミド 3−メトキシアクリラート174gを得た。
スクシンイミド 3−メトキシアクリラート
1H−NMR(CDCl3)δ(ppm):7.84(1H,d,J=12.7Hz),5.38(1H,d,J=12.4Hz),3.80(3H,s),2.84(4H,s).Reference production example 13
200 g of N-hydroxysuccinimide, 287 g of sodium 3-methoxyacrylate described in Reference Production Example 30, 528 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride, 269 g of pyridine and N, N-dimethylformamide 2 L of the mixture was stirred at room temperature for 44 hours. The reaction mixture was added to aqueous sodium hydrogen carbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate, aqueous sodium hydrogen sulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with a mixed solvent of tert-butyl methyl ether and hexane and then dried under reduced pressure to obtain 174 g of succinimide 3-methoxyacrylate.
Succinimide 3-methoxyacrylate
1 H-NMR (CDCl 3 ) δ (ppm): 7.84 (1H, d, J = 12.7 Hz), 5.38 (1H, d, J = 12.4 Hz), 3.80 (3H, s ), 2.84 (4H, s).
参考製造例14
参考製造例13に記載のスクシンイミド 3−メトキシアクリラート10g、2−メトキシフェニルヒドラジン塩酸塩7.4g、水酸化ナトリウム1.9g、ジオキサン125mLおよび水125mLの混合物を60℃で20時間加熱した。反応液を水を加え、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した後、減圧下に濃縮した。得られた残渣と濃塩酸40mLを室温で2時間攪拌した。反応液に、氷冷下で28%水酸化ナトリウム水溶液を加えた。得られた残渣をメチルtert−ブチルエーテルとヘキサンの混合溶媒で洗浄した後、減圧下に乾燥し、1−(2−メトキシフェニル)−1H−ピラゾール−3−オール3.4gを得た。
1H−NMR(CDCl3)δ(ppm):7.73(1H,d,J=2.7Hz),7.50(1H,dd,J=8.0,1.6Hz),7.26(1H,ddd,J=8.7,7.0,1.3Hz),7.07(1H,td,J=7.7,1.3Hz),7.02(1H,dd,J=8.4,1.3Hz),5.82(1H,d,J=2.5Hz),3.88(3H,s).Reference production example 14
A mixture of 10 g of succinimide 3-methoxyacrylate described in Reference Production Example 13, 7.4 g of 2-methoxyphenylhydrazine hydrochloride, 1.9 g of sodium hydroxide, 125 mL of dioxane and 125 mL of water was heated at 60 ° C. for 20 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue and 40 mL of concentrated hydrochloric acid were stirred at room temperature for 2 hours. A 28% aqueous sodium hydroxide solution was added to the reaction solution under ice cooling. The obtained residue was washed with a mixed solvent of methyl tert-butyl ether and hexane, and then dried under reduced pressure to obtain 3.4 g of 1- (2-methoxyphenyl) -1H-pyrazol-3-ol.
1 H-NMR (CDCl 3 ) δ (ppm): 7.73 (1H, d, J = 2.7 Hz), 7.50 (1H, dd, J = 8.0, 1.6 Hz), 7.26 (1H, ddd, J = 8.7, 7.0, 1.3 Hz), 7.07 (1H, td, J = 7.7, 1.3 Hz), 7.02 (1H, dd, J = 8 .4, 1.3 Hz), 5.82 (1H, d, J = 2.5 Hz), 3.88 (3H, s).
参考製造例15
エチルキサントゲン酸カリウム192.4g、クロロ酢酸ナトリウム139.8gおよび水1.1Lの混合物を25℃で8時間攪拌後、濃アンモニア水100mLを加え、さらに25℃で20時間攪拌した。反応混合物をメチルtert−ブチルエーテルで抽出した後、有機層を飽和食塩水で洗浄し、無水硫酸ナトリウムで乾燥した。減圧下に濃縮後、チオカルバミド酸O−エチルを58.7g得た。
チオカルバミド酸O−エチル
1H−NMR(CDCl3)δ:1.34(3H,t,J=7.0Hz),4.49(2H,q,J=7.0Hz),6.01(1H,s),6.40(1H,s).Reference production example 15
A mixture of 192.4 g of potassium ethyl xanthate, 139.8 g of sodium chloroacetate and 1.1 L of water was stirred at 25 ° C. for 8 hours, 100 mL of concentrated aqueous ammonia was added, and the mixture was further stirred at 25 ° C. for 20 hours. The reaction mixture was extracted with methyl tert-butyl ether, and the organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After concentration under reduced pressure, 58.7 g of O-ethyl thiocarbamate was obtained.
O-ethyl thiocarbamate
1 H-NMR (CDCl 3 ) δ: 1.34 (3H, t, J = 7.0 Hz), 4.49 (2H, q, J = 7.0 Hz), 6.01 (1H, s), 6 .40 (1H, s).
参考製造例16
1−(4−クロロフェニル)−2−ブロモ−1−エタノン10.00g、参考製造例15記載のチオカルバミド酸O−エチル4.50gおよびエタノール40mLの混合物を加熱還流下11時間加熱した。反応混合物に水を注加し、析出した固体を濾過後、水で洗浄することにより、4−(4−クロロフェニル)−2,3−ジヒドロ−2−オキソチアゾールを8.44g得た。
1H−NMR(DMSO−d6)δ:6.88(1H,d,J=1.7Hz),7.50(2H,dt,J=2.0,8.8Hz),7.68(2H,dt,J=2.2,8.8Hz),11.84(1H,s).Reference Production Example 16
A mixture of 10.00 g of 1- (4-chlorophenyl) -2-bromo-1-ethanone, 4.50 g of O-ethyl thiocarbamate described in Reference Production Example 15 and 40 mL of ethanol was heated for 11 hours while heating under reflux. Water was poured into the reaction mixture, and the precipitated solid was filtered and then washed with water to obtain 8.44 g of 4- (4-chlorophenyl) -2,3-dihydro-2-oxothiazole.
1 H-NMR (DMSO-d 6 ) δ: 6.88 (1H, d, J = 1.7 Hz), 7.50 (2H, dt, J = 2.0, 8.8 Hz), 7.68 ( 2H, dt, J = 2.2, 8.8 Hz), 11.84 (1H, s).
同様の操作により、4−(4−フルオロフェニル)−2,3−ジヒドロ−2−オキソチアゾール、4−(4−ブロモフェニル)−2,3−ジヒドロ−2−オキソチアゾール、4−(1−アダマンチル)−2,3−ジヒドロ−2−オキソチアゾールを得た。
以下に物性値を示す。By the same operation, 4- (4-fluorophenyl) -2,3-dihydro-2-oxothiazole, 4- (4-bromophenyl) -2,3-dihydro-2-oxothiazole, 4- (1- Adamantyl) -2,3-dihydro-2-oxothiazole was obtained.
The physical property values are shown below.
4−(4−フルオロフェニル)−2,3−ジヒドロ−2オキソ−チアゾール
1H−NMR(DMSO−d6)δ:6.76(1H,s),7.27(2H,t,J=8.7Hz),7.68(2H,dd,J=5.3,8.0Hz),11.77(1H,s).4- (4-Fluorophenyl) -2,3-dihydro-2oxo-thiazole
1 H-NMR (DMSO-d 6 ) δ: 6.76 (1H, s), 7.27 (2H, t, J = 8.7 Hz), 7.68 (2H, dd, J = 5.3) 8.0 Hz), 11.77 (1H, s).
4−(4−ブロモフェニル)−2,3−ジヒドロ−2−オキソチアゾール
1H−NMR(DMSO−d6)δ:6.89(1H,s),7.61(2H,d,J=8.5Hz),7.64(2H,d,J=9.2Hz),11.85(1H,s).4- (4-Bromophenyl) -2,3-dihydro-2-oxothiazole
1 H-NMR (DMSO-d 6 ) δ: 6.89 (1H, s), 7.61 (2H, d, J = 8.5 Hz), 7.64 (2H, d, J = 9.2 Hz) , 11.85 (1H, s).
4−(1−アダマンチル)−2,3−ジヒドロ−2−オキソチアゾール
1H−NMR(CDCl3)δ:1.71−1.79(6H,m),1.83(6H,d,J=2.7Hz),2.07(3H,s),5.62(1H,d,J=2.2Hz),10.01(1H,s).4- (1-adamantyl) -2,3-dihydro-2-oxothiazole
1 H-NMR (CDCl 3 ) δ: 1.71-1.79 (6H, m), 1.83 (6H, d, J = 2.7 Hz), 2.07 (3H, s), 5.62 (1H, d, J = 2.2 Hz), 10.01 (1H, s).
参考製造例17
4−メトキシ−3−メチル−安息香酸5.0g、およびテトラヒドロフラン100mlの混合物に、室温で、オキサリルクロリド4.0g、およびジメチルホルムアミド0.2mlを加え2.5時間攪拌した後、減圧下濃縮した。この混合物に、室温で、クロロホルム150ml、N,O−ジメチル−ヒドロキシルアミン−塩酸塩3.5g、およびN,N−ジイソプロピルエチルアミン9.3gを加え4時間攪拌した。水を加え、クロロホルムで抽出し、有機層を水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。残渣をカラムクロマトグラフィーに付し、4,N−ジメトキシ−3−メチル−N−メチルベンズアミド(D2Aと記す)6.1gを得た。
1H−NMR(CDCl3)δ:7.61−7.58(1H,m),7.54(1H,dd,J=2.1,0.6Hz),6.81(1H,d,J=8.5Hz),3.87(3H,s),3.57(3H,s),3.35(3H,s),2.23(3H,s).Reference Production Example 17
To a mixture of 5.0 g of 4-methoxy-3-methyl-benzoic acid and 100 ml of tetrahydrofuran was added 4.0 g of oxalyl chloride and 0.2 ml of dimethylformamide at room temperature, and the mixture was stirred for 2.5 hours and then concentrated under reduced pressure. . To this mixture, 150 ml of chloroform, 3.5 g of N, O-dimethyl-hydroxylamine-hydrochloride and 9.3 g of N, N-diisopropylethylamine were added and stirred for 4 hours at room temperature. Water was added and the mixture was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography to obtain 6.1 g of 4, N-dimethoxy-3-methyl-N-methylbenzamide (denoted as D2A).
1 H-NMR (CDCl 3 ) δ: 7.61-7.58 (1H, m), 7.54 (1H, dd, J = 2.1, 0.6 Hz), 6.81 (1H, d, J = 8.5 Hz), 3.87 (3H, s), 3.57 (3H, s), 3.35 (3H, s), 2.23 (3H, s).
参考製造例18
参考製造例17に記載のD2Aを5.7g、テトラヒドロフラン100ml、および0.95mol/Lエチルマグネシウムブロミド−テトラヒドロフラン溶液43mlの混合物を加熱還流下6時間攪拌した。室温で、飽和塩化アンモニウム水溶液を加え、酢酸エチルで抽出し、有機層を水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。残渣をカラムクロマトグラフィーに付し、1−(4−メトキシ−3−メチルフェニル)−プロパン−1−オン(D3Aと記す)4.6gを得た。
1H−NMR(CDCl3)δ:7.83(1H,dd,J=8.6,2.3Hz),7.79−7.78(1H,m),6.84(1H,d,J=8.7Hz),3.89(3H,s),2.95(2H,q,J=7.2Hz),2.25(3H,s),1.21(3H,t,J=7.2Hz).Reference Production Example 18
A mixture of 5.7 g of D2A described in Reference Production Example 17, 100 ml of tetrahydrofuran, and 43 ml of a 0.95 mol / L ethylmagnesium bromide-tetrahydrofuran solution was stirred with heating under reflux for 6 hours. A saturated aqueous ammonium chloride solution was added at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography to obtain 4.6 g of 1- (4-methoxy-3-methylphenyl) -propan-1-one (denoted as D3A).
1 H-NMR (CDCl 3 ) δ: 7.83 (1H, dd, J = 8.6, 2.3 Hz), 7.79-7.78 (1H, m), 6.84 (1H, d, J = 8.7 Hz), 3.89 (3H, s), 2.95 (2H, q, J = 7.2 Hz), 2.25 (3H, s), 1.21 (3H, t, J = 7.2 Hz).
参考製造例19
参考製造例18に記載のD3Aを5.2g、テトラヒドロフラン100ml、カリウム−tert−ブトキシド4.1g、および炭酸ジエチル3.6gの混合物を加熱還流下5.5時間攪拌した。室温で、6N−塩酸20mlを加え、酢酸エチルで抽出し、有機層を水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。残渣をカラムクロマトグラフィーに付し、3−(4−メトキシ−3−メチルフェニル)−2−メチル−3−オキソプロピオン酸エチルエステル(D4Aと記す)3.5gを得た。
1H−NMR(CDCl3)δ:7.86(1H,dd,J=8.6,2.3Hz),7.80(1H,d,J=2.2Hz),6.86(1H,d,J=8.7Hz),4.19−4.10(3H,m),3.90(3H,s),2.25(3H,s),1.47(3H,d,J=7.2Hz),1.19(3H,t,J=7.1Hz).Reference Production Example 19
A mixture of 5.2 g of D3A described in Reference Production Example 18, 100 ml of tetrahydrofuran, 4.1 g of potassium tert-butoxide, and 3.6 g of diethyl carbonate was stirred with heating under reflux for 5.5 hours. At room temperature, 20 ml of 6N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography to obtain 3.5 g of 3- (4-methoxy-3-methylphenyl) -2-methyl-3-oxopropionic acid ethyl ester (denoted as D4A).
1 H-NMR (CDCl 3 ) δ: 7.86 (1H, dd, J = 8.6, 2.3 Hz), 7.80 (1H, d, J = 2.2 Hz), 6.86 (1H, d, J = 8.7 Hz), 4.19-4.10 (3H, m), 3.90 (3H, s), 2.25 (3H, s), 1.47 (3H, d, J = 7.2 Hz), 1.19 (3H, t, J = 7.1 Hz).
参考製造例20
参考製造例19に記載のD4Aを3.5g、トルエン100ml、およびメチルヒドラジン7.4gの混合物を加熱還流下18時間攪拌した。トルエンを留去し、3N塩酸水溶液を加え、沈殿物をろ過、ヘキサンで洗浄し、3−(4−メトキシ−3−メチルフェニル)−1,4−ジメチル−5−ヒドロキシ−1H−ピラゾール(D5Aと記す)1.4gを得た。
1H−NMR(DMSO−D6)δ:7.47−7.44(2H,m),7.07(1H,d,J=8.2Hz),3.84(3H,s),3.66(3H,s),2.20(3H,s),2.05(3H,s).Reference Production Example 20
A mixture of 3.5 g of D4A described in Reference Production Example 19, 100 ml of toluene, and 7.4 g of methylhydrazine was stirred with heating under reflux for 18 hours. Toluene was distilled off, 3N aqueous hydrochloric acid was added, the precipitate was filtered and washed with hexane to give 3- (4-methoxy-3-methylphenyl) -1,4-dimethyl-5-hydroxy-1H-pyrazole (D5A). 1.4g was obtained.
1 H-NMR (DMSO-D 6 ) δ: 7.47-7.44 (2H, m), 7.07 (1H, d, J = 8.2 Hz), 3.84 (3H, s), 3 .66 (3H, s), 2.20 (3H, s), 2.05 (3H, s).
参考製造例21
参考製造例20に記載のD5Aを1.4g、およびオキシ塩化リン31.8gの混合物を100℃で11時間攪拌した。減圧下濃縮し、酢酸エチルで抽出し、有機層を水で洗浄し、無水硫酸マグネシウムで乾燥した後、減圧下濃縮した。残渣をカラムクロマトグラフィーに付し、5−クロロ−3−(4−メトキシ−3−メチルフェニル)−1,4−ジメチル−1H−ピラゾール(D6Aと記す)0.4gを得た。
1H−NMR(DMSO−D6)δ:7.42−7.40(2H,m),6.98(1H,d,J=9.2Hz),3.81(3H,s),3.80(3H,s),2.19(3H,s),2.11(3H,s).Reference Production Example 21
A mixture of 1.4 g of D5A described in Reference Production Example 20 and 31.8 g of phosphorus oxychloride was stirred at 100 ° C. for 11 hours. The mixture was concentrated under reduced pressure, extracted with ethyl acetate, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography to obtain 0.4 g of 5-chloro-3- (4-methoxy-3-methylphenyl) -1,4-dimethyl-1H-pyrazole (denoted as D6A).
1 H-NMR (DMSO-D 6 ) δ: 7.42-7.40 (2H, m), 6.98 (1H, d, J = 9.2 Hz), 3.81 (3H, s), 3 .80 (3H, s), 2.19 (3H, s), 2.11 (3H, s).
参考製造例22
参考製造例21に記載のD6Aを0.4g、47%臭化水素酸3ml、および酢酸3mlの混合物を加熱還流下、15時間攪拌した。反応液を減圧濃縮した後、残査に酢酸エチルを20ml加え、室温で1時間攪拌した。沈殿物を濾過し、ヘキサンで洗浄後、減圧下乾燥し、4−(5−クロロ−1,4−ジメチル−1H−ピラゾール−3−イル)−2−メチルフェノール0.3gを得た。
1H−NMR(DMSO−D6)δ:7.33(1H,s),7.24(1H,d,J=8.2Hz),6.83(1H,d,J=8.2Hz),3.78(3H,s),2.15(3H,s),2.09(3H,s).Reference Production Example 22
A mixture of 0.4 g of D6A described in Reference Production Example 21, 3 ml of 47% hydrobromic acid, and 3 ml of acetic acid was stirred with heating under reflux for 15 hours. The reaction solution was concentrated under reduced pressure, 20 ml of ethyl acetate was added to the residue, and the mixture was stirred at room temperature for 1 hour. The precipitate was filtered, washed with hexane, and dried under reduced pressure to obtain 0.3 g of 4- (5-chloro-1,4-dimethyl-1H-pyrazol-3-yl) -2-methylphenol.
1 H-NMR (DMSO-D 6 ) δ: 7.33 (1H, s), 7.24 (1H, d, J = 8.2 Hz), 6.83 (1H, d, J = 8.2 Hz) , 3.78 (3H, s), 2.15 (3H, s), 2.09 (3H, s).
上記の方法に準じて化合物、HA1001−001〜HA3292−7660(以下、本化合物Aと記す。)を得ることができる。
上記化合物HA1001−001〜HA3292−7660は、
A compound, HA1001-001 to HA3292-7660 (hereinafter referred to as the present compound A) can be obtained according to the above method.
The compounds HA1001-001 to HA3292-7660 are
〔式中、Tは、以下に示す置換基番号1〜7660に各々対応する置換基〕で示されるテトラゾリノン化合物である。また、下記の[置換基番号;T]に記載の2−Pyはピリジン−2−イルを表し、3−Pyはピリジン−3−イルを表し、4−Pyはピリジン−4−イルを表し、Fはフルオロを表し、Clはクロロを表し、Brはブロモを表し、Iはヨードを表し、CNはシアノを表し、Meはメチルを表し、Etはエチルを表し、Prはプロピルを表し、i−Prはイソプロピル基を表し、CF3はトリフルオロメチルを表し、CH2CF3は2,2,2−トリフルオロエチルを表し、CHF2はジフルオロメチルを表し、OMeはメトキシを表し、OCH2CF3は2,2,2−トリフルオロエトキシを表し、OEtはエトキシを表し、OPrはプロポキシを表し、i−OPrはイソプロポキシを表し、OCF3はトリフルオロメトキシを表し、OCHF2はジフルオロメトキシを表し、SMeはメチルチオを表し、S(O)Meはメチルスルフィニルを表し、S(O)2Meはメチルスルホニルを表し、SCF3はトリフルオロメチルチオを表し、S(O)CF3はトリフルオロメチルスルフィニルを表し、S(O)2CF3はトリフルオロメチルスルホニルを表し、COOMeはメトキシカルボニルを表し、NO2はニトロを表し、NH2はアミノを表し、NHMeはメチルアミノを表し、NMe2はジメチルアミノを表し、ACはアセチルを表し、ACNHはアセチルアミノを表し、N−AC−N−Me−NはN−アセチル−N−メチルアミノを表し、PYR1はピラゾール−1−イル基を表し、PYR3はピラゾール−3−イル基を表し、Phはフェニルを表し、diはジを表し、triはトリを表す。 [Wherein, T represents a substituent corresponding to each of substituent numbers 1 to 7660 shown below]. Further, 2-Py described in [Substituent No .; T] below represents pyridin-2-yl, 3-Py represents pyridin-3-yl, 4-Py represents pyridin-4-yl, F represents fluoro, Cl represents chloro, Br represents bromo, I represents iodo, CN represents cyano, Me represents methyl, Et represents ethyl, Pr represents propyl, i- Pr represents an isopropyl group, CF3 represents trifluoromethyl, CH2CF3 represents 2,2,2-trifluoroethyl, CHF2 represents difluoromethyl, OMe represents methoxy, OCH2CF3 represents 2,2,2- Represents trifluoroethoxy, OEt represents ethoxy, OPr represents propoxy, i-OPr represents isopropoxy, OCF3 represents trifluoromethoxy, OCH 2 represents difluoromethoxy, SMe represents methylthio, S (O) Me represents methylsulfinyl, S (O) 2Me represents methylsulfonyl, SCF3 represents trifluoromethylthio, S (O) CF3 represents tri Represents fluoromethylsulfinyl, S (O) 2CF3 represents trifluoromethylsulfonyl, COOMe represents methoxycarbonyl, NO2 represents nitro, NH2 represents amino, NHMe represents methylamino, NMe2 represents dimethylamino AC represents acetyl, ACNH represents acetylamino, N-AC-N-Me-N represents N-acetyl-N-methylamino, PYR1 represents a pyrazol-1-yl group, PYR3 represents pyrazole Represents a -3-yl group, Ph represents phenyl, di represents di, t i represents the birds.
例えば、HA1001−0001とは、式(H1001)で表される化合物においてTが置換基番号0001である化合物を表し、下記式で表される。
For example, HA1001-0001 represents a compound represented by the formula (H1001), in which T is substituent number 0001, and is represented by the following formula.
[0001:2−Py]、[0002:3−F−2−Py]、[0003:4−Cl−3−F−2−Py]、[0004:5−Cl−3−F−2−Py]、[0005:6−Cl−3−F−2−Py]、[0006:4−Me−3−F−2−Py]、[0007:5−Me−3−F−2−Py]、[0008:6−Me−3−F−2−Py]、[0009:4−CF3−3−F−2−Py]、[0010:5−CF3−3−F−2−Py]、[0011:6−CF3−3−F−2−Py]、[0012:4−CN−3−F−2−Py]、[0013:5−CN−3−F−2−Py]、[0014:6−CN−3−F−2−Py]、[0015:4−OMe−3−F−2−Py]、[0016:5−OMe−3−F−2−Py]、[0017:6−OMe−3−F−2−Py]、[0018:4−F−2−Py]、[0019:3−Cl−4−F−2−Py]、[0020:5−Cl−4−F−2−Py]、[0021:6−Cl−4−F−2−Py]、[0022:3−Me−4−F−2−Py]、[0023:5−Me−4−F−2−Py]、[0024:6−Me−4−F−2−Py]、[0025:3−CF3−4−F−2−Py]、[0026:5−CF3−4−F−2−Py]、[0027:6−CF3−4−F−2−Py]、[0028:3−CN−4−F−2−Py]、[0029:5−CN−4−F−2−Py]、[0030:6−CN−4−F−2−Py]、[0031:3−OMe−4−F−2−Py]、[0032:5−OMe−4−F−2−Py]、[0033:6−OMe−4−F−2−Py]、[0034:5−F−2−Py]、[0035:3−Cl−5−F−2−Py]、[0036:4−Cl−5−F−2−Py]、[0037:6−Cl−5−F−2−Py]、[0038:3−Me−5−F−2−Py]、[0039:4−Me−5−F−2−Py]、[0040:6−Me−5−F−2−Py]、[0041:3−CF3−5−F−2−Py]、[0042:4−CF3−5−F−2−Py]、[0043:6−CF3−5−F−2−Py]、[0044:3−CN−5−F−2−Py]、[0045:4−CN−5−F−2−Py]、[0046:6−CN−5−F−2−Py]、[0047:3−OMe−5−F−2−Py]、[0048:4−OMe−5−F−2−Py]、[0049:6−OMe−5−F−2−Py]、[0050:6−F−2−Py]、[0051:3−Cl−6−F−2−Py]、[0052:4−Cl−6−F−2−Py]、[0053:5−Cl−6−F−2−Py]、[0054:3−Me−6−F−2−Py]、[0055:4−Me−6−F−2−Py]、[0056:5−Me−6−F−2−Py]、[0057:3−CF3−6−F−2−Py]、[0058:4−CF3−6−F−2−Py]、[0059:5−CF3−6−F−2−Py]、[0060:3−CN−6−F−2−Py]、[0061:4−CN−6−F−2−Py]、[0062:5−CN−6−F−2−Py]、[0063:3−OMe−6−F−2−Py]、[0064:4−OMe−6−F−2−Py]、[0065:5−OMe−6−F−2−Py]、[0066:3−Cl−2−Py]、[0067:4−Cl−3−Cl−2−Py]、[0068:5−Cl−3−Cl−2−Py]、[0069:6−Cl−3−Cl−2−Py]、[0070:4−Me−3−Cl−2−Py]、[0071:5−Me−3−Cl−2−Py]、[0072:6−Me−3−Cl−2−Py]、[0073:4−CF3−3−Cl−2−Py]、[0074:5−CF3−3−Cl−2−Py]、[0075:6−CF3−3−Cl−2−Py]、[0076:4−CN−3−Cl−2−Py]、[0077:5−CN−3−Cl−2−Py]、[0078:6−CN−3−Cl−2−Py]、[0079:4−OMe−3−Cl−2−Py]、[0080:5−OMe−3−Cl−2−Py]、[0081:6−OMe−3−Cl−2−Py]、[0082:4−Cl−2−Py]、[0083:3−Cl−4−Cl−2−Py]、[0084:5−Cl−4−Cl−2−Py]、[0085:6−Cl−4−Cl−2−Py]、[0086:3−Me−4−Cl−2−Py]、[0087:5−Me−4−Cl−2−Py]、[0088:6−Me−4−Cl−2−Py]、[0089:3−CF3−4−Cl−2−Py]、[0090:5−CF3−4−Cl−2−Py]、[0091:6−CF3−4−Cl−2−Py]、[0092:3−CN−4−Cl−2−Py]、[0093:5−CN−4−Cl−2−Py]、[0094:6−CN−4−Cl−2−Py]、[0095:3−OMe−4−Cl−2−Py]、[0096:5−OMe−4−Cl−2−Py]、[0097:6−OMe−4−Cl−2−Py]、[0098:5−Cl−2−Py]、[0099:4−Cl−5−Cl−2−Py]、[0100:5−Cl−5−Cl−2−Py]、 [0001: 2-Py], [0002: 3-F-2-Py], [0003: 4-Cl-3-F-2-Py], [0004: 5-Cl-3-F-2-Py] ], [0005: 6-Cl-3-F-2-Py], [0006: 4-Me-3-F-2-Py], [0007: 5-Me-3-F-2-Py], [0008: 6-Me-3-F-2-Py], [0009: 4-CF3-3-F-2-Py], [0010: 5-CF3-3-F-2-Py], [0011] : 6-CF3-3-F-2-Py], [0012: 4-CN-3-F-2-Py], [0013: 5-CN-3-F-2-Py], [0014: 6 -CN-3-F-2-Py], [0015: 4-OMe-3-F-2-Py], [0016: 5-OMe-3-F-2-Py], [0017: -OMe-3-F-2-Py], [0018: 4-F-2-Py], [0019: 3-Cl-4-F-2-Py], [0020: 5-Cl-4-F -2-Py], [0021: 6-Cl-4-F-2-Py], [0022: 3-Me-4-F-2-Py], [0023: 5-Me-4-F-2 -Py], [0024: 6-Me-4-F-2-Py], [0025: 3-CF3-4-F-2-Py], [0026: 5-CF3-4-F-2-Py ], [0027: 6-CF3-4-F-2-Py], [0028: 3-CN-4-F-2-Py], [0029: 5-CN-4-F-2-Py], [0030: 6-CN-4-F-2-Py], [0031: 3-OMe-4-F-2-Py], [0032: 5-OMe-4-F-2-Py], [0 33: 6-OMe-4-F-2-Py], [0034: 5-F-2-Py], [0035: 3-Cl-5-F-2-Py], [0036: 4-Cl- 5-F-2-Py], [0037: 6-Cl-5-F-2-Py], [0038: 3-Me-5-F-2-Py], [0039: 4-Me-5- F-2-Py], [0040: 6-Me-5-F-2-Py], [0041: 3-CF3-5-F-2-Py], [0042: 4-CF3-5-F- 2-Py], [0043: 6-CF3-5-F-2-Py], [0044: 3-CN-5-F-2-Py], [0045: 4-CN-5-F-2- Py], [0046: 6-CN-5-F-2-Py], [0047: 3-OMe-5-F-2-Py], [0048: 4-OMe-5-F-2-Py] , [0049: 6-OMe-5-F-2-Py], [0050: 6-F-2-Py], [0051: 3-Cl-6-F-2-Py], [0052: 4- Cl-6-F-2-Py], [0053: 5-Cl-6-F-2-Py], [0054: 3-Me-6-F-2-Py], [0055: 4-Me- 6-F-2-Py], [0056: 5-Me-6-F-2-Py], [0057: 3-CF3-6-F-2-Py], [0058: 4-CF3-6 F-2-Py], [0059: 5-CF3-6-F-2-Py], [0060: 3-CN-6-F-2-Py], [0061: 4-CN-6-F- 2-Py], [0062: 5-CN-6-F-2-Py], [0063: 3-OMe-6-F-2-Py], [0064: 4-OMe-6-F-2 Py], [0065: 5-OMe-6-F-2-Py], [0066: 3-Cl-2-Py], [0067: 4-Cl-3-Cl-2-Py], [0068: 5-Cl-3-Cl-2-Py], [0069: 6-Cl-3-Cl-2-Py], [0070: 4-Me-3-Cl-2-Py], [0071: 5- Me-3-Cl-2-Py], [0072: 6-Me-3-Cl-2-Py], [0073: 4-CF3-3-Cl-2-Py], [0074: 5-CF3- 3-Cl-2-Py], [0075: 6-CF3-3-Cl-2-Py], [0076: 4-CN-3-Cl-2-Py], [0077: 5-CN-3- Cl-2-Py], [0078: 6-CN-3-Cl-2-Py], [0079: 4-OMe-3-Cl-2-Py] [0080: 5-OMe-3-Cl-2-Py], [0081: 6-OMe-3-Cl-2-Py], [0082: 4-Cl-2-Py], [0083: 3-Cl -4-Cl-2-Py], [0084: 5-Cl-4-Cl-2-Py], [0085: 6-Cl-4-Cl-2-Py], [0086: 3-Me-4 -Cl-2-Py], [0087: 5-Me-4-Cl-2-Py], [0088: 6-Me-4-Cl-2-Py], [0089: 3-CF3-4-Cl -2-Py], [0090: 5-CF3-4-Cl-2-Py], [0091: 6-CF3-4-Cl-2-Py], [0092: 3-CN-4-Cl-2 -Py], [0093: 5-CN-4-Cl-2-Py], [0094: 6-CN-4-Cl-2-Py], [00 95: 3-OMe-4-Cl-2-Py], [0096: 5-OMe-4-Cl-2-Py], [0097: 6-OMe-4-Cl-2-Py], [0098: 5-Cl-2-Py], [0099: 4-Cl-5-Cl-2-Py], [0100: 5-Cl-5-Cl-2-Py],
[0101:6−Cl−5−Cl−2−Py]、[0102:4−Me−5−Cl−2−Py]、[0103:5−Me−5−Cl−2−Py]、[0104:6−Me−5−Cl−2−Py]、[0105:4−CF3−5−Cl−2−Py]、[0106:5−CF3−5−Cl−2−Py]、[0107:6−CF3−5−Cl−2−Py]、[0108:4−CN−5−Cl−2−Py]、[0109:3−CN−5−Cl−2−Py]、[0110:6−CN−5−Cl−2−Py]、[0111:4−OMe−5−Cl−2−Py]、[0112:5−OMe−5−Cl−2−Py]、[0113:6−OMe−5−Cl−2−Py]、[0114:6−Cl−2−Py]、[0115:3−Cl−6−Cl−2−Py]、[0116:4−Cl−6−Cl−2−Py]、[0117:5−Cl−6−Cl−2−Py]、[0118:3−Me−6−Cl−2−Py]、[0119:4−Me−6−Cl−2−Py]、[0120:5−Me−6−Cl−2−Py]、[0121:3−CF3−6−Cl−2−Py]、[0122:4−CF3−6−Cl−2−Py]、[0123:5−CF3−6−Cl−2−Py]、[0124:3−CN−6−Cl−2−Py]、[0125:4−CN−6−Cl−2−Py]、[0126:5−CN−6−Cl−2−Py]、[0127:3−OMe−6−Cl−2−Py]、[0128:4−OMe−6−Cl−2−Py]、[0129:5−OMe−6−Cl−2−Py]、[0130:3−Br−2−Py]、[0131:4−Cl−3−Br−2−Py]、[0132:5−Cl−3−Br−2−Py]、[0133:6−Cl−3−Br−2−Py]、[0134:4−Me−3−Br−2−Py]、[0135:5−Me−3−Br−2−Py]、[0136:6−Me−3−Br−2−Py]、[0137:4−CF3−3−Br−2−Py]、[0138:5−CF3−3−Br−2−Py]、[0139:6−CF3−3−Br−2−Py]、[0140:4−CN−3−Br−2−Py]、[0141:5−CN−3−Br−2−Py]、[0142:6−CN−3−Br−2−Py]、[0143:4−OMe−3−Br−2−Py]、[0144:5−OMe−3−Br−2−Py]、[0145:6−OMe−3−Br−2−Py]、[0146:4−Br−2−Py]、[0147:3−Cl−4−Br−2−Py]、[0148:5−Cl−4−Br−2−Py]、[0149:6−Cl−4−Br−2−Py]、[0150:3−Me−4−Br−2−Py]、[0151:5−Me−4−Br−2−Py]、[0152:6−Me−4−Br−2−Py]、[0153:3−CF3−4−Br−2−Py]、[0154:5−CF3−4−Br−2−Py]、[0155:6−CF3−4−Br−2−Py]、[0156:3−CN−4−Br−2−Py]、[0157:5−CN−4−Br−2−Py]、[0158:6−CN−4−Br−2−Py]、[0159:3−OMe−4−Br−2−Py]、[0160:5−OMe−4−Br−2−Py]、[0161:6−OMe−4−Br−2−Py]、[0162:5−Br−2−Py]、[0163:3−Cl−5−Br−2−Py]、[0164:4−Cl−5−Br−2−Py]、[0165:6−Cl−5−Br−2−Py]、[0166:3−Me−5−Br−2−Py]、[0167:4−Me−5−Br−2−Py]、[0168:6−Me−5−Br−2−Py]、[0169:3−CF3−5−Br−2−Py]、[0170:4−CF3−5−Br−2−Py]、[0171:6−CF3−5−Br−2−Py]、[0172:3−CN−5−Br−2−Py]、[0173:4−CN−5−Br−2−Py]、[0174:6−CN−5−Br−2−Py]、[0175:3−OMe−5−Br−2−Py]、[0176:4−OMe−5−Br−2−Py]、[0177:6−OMe−5−Br−2−Py]、[0178:6−Br−2−Py]、[0179:3−Cl−6−Br−2−Py]、[0180:4−Cl−6−Br−2−Py]、[0181:5−Cl−6−Br−2−Py]、[0182:3−Me−6−Br−2−Py]、[0183:4−Me−6−Br−2−Py]、[0184:5−Me−6−Br−2−Py]、[0185:3−CF3−6−Br−2−Py]、[0186:4−CF3−6−Br−2−Py]、[0187:5−CF3−6−Br−2−Py]、[0188:3−CN−6−Br−2−Py]、[0189:4−CN−6−Br−2−Py]、[0190:5−CN−6−Br−2−Py]、[0191:3−OMe−6−Br−2−Py]、[0192:4−OMe−6−Br−2−Py]、[0193:5−OMe−6−Br−2−Py]、[0194:3−I−2−Py]、[0195:4−Cl−3−I−2−Py]、[0196:5−Cl−3−I−2−Py]、[0197:6−Cl−3−I−2−Py]、[0198:4−Me−3−I−2−Py]、[0199:5−Me−3−I−2−Py]、[0200:6−Me−3−I−2−Py]、 [0101: 6-Cl-5-Cl-2-Py], [0102: 4-Me-5-Cl-2-Py], [0103: 5-Me-5-Cl-2-Py], [0104 : 6-Me-5-Cl-2-Py], [0105: 4-CF3-5-Cl-2-Py], [0106: 5-CF3-5-Cl-2-Py], [0107: 6 -CF3-5-Cl-2-Py], [0108: 4-CN-5-Cl-2-Py], [0109: 3-CN-5-Cl-2-Py], [0110: 6-CN -5-Cl-2-Py], [0111: 4-OMe-5-Cl-2-Py], [0112: 5-OMe-5-Cl-2-Py], [0113: 6-OMe-5. -Cl-2-Py], [0114: 6-Cl-2-Py], [0115: 3-Cl-6-Cl-2-Py], [0 16: 4-Cl-6-Cl-2-Py], [0117: 5-Cl-6-Cl-2-Py], [0118: 3-Me-6-Cl-2-Py], [0119: 4-Me-6-Cl-2-Py], [0120: 5-Me-6-Cl-2-Py], [0121: 3-CF3-6-Cl-2-Py], [0122: 4- CF3-6-Cl-2-Py], [0123: 5-CF3-6-Cl-2-Py], [0124: 3-CN-6-Cl-2-Py], [0125: 4-CN- 6-Cl-2-Py], [0126: 5-CN-6-Cl-2-Py], [0127: 3-OMe-6-Cl-2-Py], [0128: 4-OMe-6-6 Cl-2-Py], [0129: 5-OMe-6-Cl-2-Py], [0130: 3-Br-2-Py], [013 : 4-Cl-3-Br-2-Py], [0132: 5-Cl-3-Br-2-Py], [0133: 6-Cl-3-Br-2-Py], [0134: 4 -Me-3-Br-2-Py], [0135: 5-Me-3-Br-2-Py], [0136: 6-Me-3-Br-2-Py], [0137: 4-CF3 -3-Br-2-Py], [0138: 5-CF3-3-3-Br-2-Py], [0139: 6-CF3-3-Br-2-Py], [0140: 4-CN-3 -Br-2-Py], [0141: 5-CN-3-Br-2-Py], [0142: 6-CN-3-Br-2-Py], [0143: 4-OMe-3-Br -2-Py], [0144: 5-OMe-3-Br-2-Py], [0145: 6-OMe-3-Br-2-Py], [0 146: 4-Br-2-Py], [0147: 3-Cl-4-Br-2-Py], [0148: 5-Cl-4-Br-2-Py], [0149: 6-Cl- 4-Br-2-Py], [0150: 3-Me-4-Br-2-Py], [0151: 5-Me-4-Br-2-Py], [0152: 6-Me-4- Br-2-Py], [0153: 3-CF3-4-Br-2-Py], [0154: 5-CF3-4-Br-2-Py], [0155: 6-CF3-4-Br- 2-Py], [0156: 3-CN-4-Br-2-Py], [0157: 5-CN-4-Br-2-Py], [0158: 6-CN-4-Br-2- Py], [0159: 3-OMe-4-Br-2-Py], [0160: 5-OMe-4-Br-2-Py], [0161 6-OMe-4-Br-2-Py], [0162: 5-Br-2-Py], [0163: 3-Cl-5-Br-2-Py], [0164: 4-Cl-5 Br-2-Py], [0165: 6-Cl-5-Br-2-Py], [0166: 3-Me-5-Br-2-Py], [0167: 4-Me-5-Br- 2-Py], [0168: 6-Me-5-Br-2-Py], [0169: 3-CF3-5-Br-2-Py], [0170: 4-CF3-5-Br-2-] Py], [0171: 6-CF3-5-Br-2-Py], [0172: 3-CN-5-Br-2-Py], [0173: 4-CN-5-Br-2-Py] [0174: 6-CN-5-Br-2-Py], [0175: 3-OMe-5-Br-2-Py], [0176: 4- Me-5-Br-2-Py], [0177: 6-OMe-5-Br-2-Py], [0178: 6-Br-2-Py], [0179: 3-Cl-6-Br- 2-Py], [0180: 4-Cl-6-Br-2-Py], [0181: 5-Cl-6-Br-2-Py], [0182: 3-Me-6-Br-2- Py], [0183: 4-Me-6-Br-2-Py], [0184: 5-Me-6-Br-2-Py], [0185: 3-CF3-6-Br-2-Py] [0186: 4-CF3-6-Br-2-Py], [0187: 5-CF3-6-Br-2-Py], [0188: 3-CN-6-Br-2-Py], [ 0189: 4-CN-6-Br-2-Py], [0190: 5-CN-6-Br-2-Py], [0191: 3-OMe- 6-Br-2-Py], [0192: 4-OMe-6-Br-2-Py], [0193: 5-OMe-6-Br-2-Py], [0194: 3-I-2- Py], [0195: 4-Cl-3-I-2-Py], [0196: 5-Cl-3-I-2-Py], [0197: 6-Cl-3-I-2-Py] [0198: 4-Me-3-I-2-Py], [0199: 5-Me-3-I-2-Py], [0200: 6-Me-3-I-2-Py],
[0201:4−CF3−3−I−2−Py]、[0202:5−CF3−3−I−2−Py]、[0203:6−CF3−3−I−2−Py]、[0204:4−CN−3−I−2−Py]、[0205:5−CN−3−I−2−Py]、[0206:6−CN−3−I−2−Py]、[0207:4−OMe−3−I−2−Py]、[0208:5−OMe−3−I−2−Py]、[0209:6−OMe−3−I−2−Py]、[0210:4−I−2−Py]、[0211:3−Cl−4−I−2−Py]、[0212:5−Cl−4−I−2−Py]、[0213:6−Cl−4−I−2−Py]、[0214:3−Me−4−I−2−Py]、[0215:5−Me−4−I−2−Py]、[0216:6−Me−4−I−2−Py]、[0217:3−CF3−4−I−2−Py]、[0218:5−CF3−4−I−2−Py]、[0219:6−CF3−4−I−2−Py]、[0220:3−CN−4−I−2−Py]、[0221:5−CN−4−I−2−Py]、[0222:6−CN−4−I−2−Py]、[0223:3−OMe−4−I−2−Py]、[0224:5−OMe−4−I−2−Py]、[0225:6−OMe−4−I−2−Py]、[0226:5−I−2−Py]、[0227:3−Cl−5−I−2−Py]、[0228:4−Cl−5−I−2−Py]、[0229:6−Cl−5−I−2−Py]、[0230:3−Me−5−I−2−Py]、[0231:4−Me−5−I−2−Py]、[0232:6−Me−5−I−2−Py]、[0233:3−CF3−5−I−2−Py]、[0234:4−CF3−5−I−2−Py]、[0235:6−CF3−5−I−2−Py]、[0236:3−CN−5−I−2−Py]、[0237:4−CN−5−I−2−Py]、[0238:6−CN−5−I−2−Py]、[0239:3−OMe−5−I−2−Py]、[0240:4−OMe−5−I−2−Py]、[0241:6−OMe−5−I−2−Py]、[0242:6−I−2−Py]、[0243:3−Cl−6−I−2−Py]、[0244:4−Cl−6−I−2−Py]、[0245:5−Cl−6−I−2−Py]、[0246:3−Me−6−I−2−Py]、[0247:4−Me−6−I−2−Py]、[0248:5−Me−6−I−2−Py]、[0249:3−CF3−6−I−2−Py]、[0250:4−CF3−6−I−2−Py]、[0251:5−CF3−6−I−2−Py]、[0252:3−CN−6−I−2−Py]、[0253:4−CN−6−I−2−Py]、[0254:5−CN−6−I−2−Py]、[0255:3−OMe−6−I−2−Py]、[0256:4−OMe−6−I−2−Py]、[0257:5−OMe−6−I−2−Py]、[0258:3−Me−2−Py]、[0259:4−Cl−3−Me−2−Py]、[0260:5−Cl−3−Me−2−Py]、[0261:6−Cl−3−Me−2−Py]、[0262:4−Me−3−Me−2−Py]、[0263:5−Me−3−Me−2−Py]、[0264:6−Me−3−Me−2−Py]、[0265:4−CF3−3−Me−2−Py]、[0266:5−CF3−3−Me−2−Py]、[0267:6−CF3−3−Me−2−Py]、[0268:4−CN−3−Me−2−Py]、[0269:5−CN−3−Me−2−Py]、[0270:6−CN−3−Me−2−Py]、[0271:4−OMe−3−Me−2−Py]、[0272:5−OMe−3−Me−2−Py]、[0273:6−OMe−3−Me−2−Py]、[0274:4−Me−2−Py]、[0275:3−Cl−4−Me−2−Py]、[0276:5−Cl−4−Me−2−Py]、[0277:6−Cl−4−Me−2−Py]、[0278:3−Me−4−Me−2−Py]、[0279:5−Me−4−Me−2−Py]、[0280:6−Me−4−Me−2−Py]、[0281:3−CF3−4−Me−2−Py]、[0282:5−CF3−4−Me−2−Py]、[0283:6−CF3−4−Me−2−Py]、[0284:3−CN−4−Me−2−Py]、[0285:5−CN−4−Me−2−Py]、[0286:6−CN−4−Me−2−Py]、[0287:3−OMe−4−Me−2−Py]、[0288:5−OMe−4−Me−2−Py]、[0289:6−OMe−4−Me−2−Py]、[0290:5−Me−2−Py]、[0291:3−Cl−5−Me−2−Py]、[0292:4−Cl−5−Me−2−Py]、[0293:6−Cl−5−Me−2−Py]、[0294:3−Me−5−Me−2−Py]、[0295:4−Me−5−Me−2−Py]、[0296:6−Me−5−Me−2−Py]、[0297:3−CF3−5−Me−2−Py]、[0298:4−CF3−5−Me−2−Py]、[0299:6−CF3−5−Me−2−Py]、[0300:3−CN−5−Me−2−Py]、 [0201: 4-CF3-3-1-I-2-Py], [0202: 5-CF3-3-1-I-2-Py], [0203: 6-CF3-3-3-I-2-Py], [0204] : 4-CN-3-I-2-Py], [0205: 5-CN-3-I-2-Py], [0206: 6-CN-3-I-2-Py], [0207: 4 -OMe-3-I-2-Py], [0208: 5-OMe-3-I-2-Py], [0209: 6-OMe-3-I-2-Py], [0210: 4-I -2-Py], [0211: 3-Cl-4-I-2-Py], [0212: 5-Cl-4-I-2-Py], [0213: 6-Cl-4-I-2 -Py], [0214: 3-Me-4-I-2-Py], [0215: 5-Me-4-I-2-Py], [0216: 6-Me-4-I-2- y], [0217: 3-CF3-4-I-2-Py], [0218: 5-CF3-4-I-2-Py], [0219: 6-CF3-4-I-2-Py] [0220: 3-CN-4-I-2-Py], [0221: 5-CN-4-I-2-Py], [0222: 6-CN-4-I-2-Py], [ 0223: 3-OMe-4-I-2-Py], [0224: 5-OMe-4-I-2-Py], [0225: 6-OMe-4-I-2-Py], [0226: 5-I-2-Py], [0227: 3-Cl-5-I-2-Py], [0228: 4-Cl-5-I-2-Py], [0229: 6-Cl-5 I-2-Py], [0230: 3-Me-5-I-2-Py], [0231: 4-Me-5-I-2-Py], [0232: 6-Me-5- -2-Py], [0233: 3-CF3-5-I-2-Py], [0234: 4-CF3-5-I-2-Py], [0235: 6-CF3-5-I-2 -Py], [0236: 3-CN-5-I-2-Py], [0237: 4-CN-5-I-2-Py], [0238: 6-CN-5-I-2-Py ], [0239: 3-OMe-5-I-2-Py], [0240: 4-OMe-5-I-2-Py], [0241: 6-OMe-5-I-2-Py], [0242: 6-I-2-Py], [0243: 3-Cl-6-I-2-Py], [0244: 4-Cl-6-I-2-Py], [0245: 5-Cl -6-I-2-Py], [0246: 3-Me-6-I-2-Py], [0247: 4-Me-6-I-2-Py], [0248: 5-Me -6-I-2-Py], [0249: 3-CF3-6-I-2-Py], [0250: 4-CF3-6-I-2-Py], [0251: 5-CF3-6. -I-2-Py], [0252: 3-CN-6-I-2-Py], [0253: 4-CN-6-I-2-Py], [0254: 5-CN-6-I -2-Py], [0255: 3-OMe-6-I-2-Py], [0256: 4-OMe-6-I-2-Py], [0257: 5-OMe-6-I-2 -Py], [0258: 3-Me-2-Py], [0259: 4-Cl-3-Me-2-Py], [0260: 5-Cl-3-Me-2-Py], [0261 : 6-Cl-3-Me-2-Py], [0262: 4-Me-3-Me-2-Py], [0263: 5-Me-3-Me-2-Py], 0264: 6-Me-3-Me-2-Py], [0265: 4-CF3-3-Me-2-Py], [0266: 5-CF3-3-Me-2-Py], [0267: 6-CF3-3-Me-2-Py], [0268: 4-CN-3-Me-2-Py], [0269: 5-CN-3-Me-2-Py], [0270: 6- CN-3-Me-2-Py], [0271: 4-OMe-3-Me-2-Py], [0272: 5-OMe-3-Me-2-Py], [0273: 6-OMe- 3-Me-2-Py], [0274: 4-Me-2-Py], [0275: 3-Cl-4-Me-2-Py], [0276: 5-Cl-4-Me-2-] Py], [0277: 6-Cl-4-Me-2-Py], [0278: 3-Me-4-Me-2-Py], [0 79: 5-Me-4-Me-2-Py], [0280: 6-Me-4-Me-2-Py], [0281: 3-CF3-4-Me-2-Py], [0282: 5-CF3-4-Me-2-Py], [0283: 6-CF3-4-Me-2-Py], [0284: 3-CN-4-Me-2-Py], [0285: 5- CN-4-Me-2-Py], [0286: 6-CN-4-Me-2-Py], [0287: 3-OMe-4-Me-2-Py], [0288: 5-OMe- 4-Me-2-Py], [0289: 6-OMe-4-Me-2-Py], [0290: 5-Me-2-Py], [0291: 3-Cl-5-Me-2-] Py], [0292: 4-Cl-5-Me-2-Py], [0293: 6-Cl-5-Me-2-Py], [0294 : 3-Me-5-Me-2-Py], [0295: 4-Me-5-Me-2-Py], [0296: 6-Me-5-Me-2-Py], [0297: 3 -CF3-5-Me-2-Py], [0298: 4-CF3-5-Me-2-Py], [0299: 6-CF3-5-Me-2-Py], [0300: 3-CN -5-Me-2-Py],
[0301:4−CN−5−Me−2−Py]、[0302:6−CN−5−Me−2−Py]、[0303:3−OMe−5−Me−2−Py]、[0304:4−OMe−5−Me−2−Py]、[0305:6−OMe−5−Me−2−Py]、[0306:6−Me−2−Py]、[0307:3−Cl−6−Me−2−Py]、[0308:4−Cl−6−Me−2−Py]、[0309:5−Cl−6−Me−2−Py]、[0310:3−Me−6−Me−2−Py]、[0311:4−Me−6−Me−2−Py]、[0312:5−Me−6−Me−2−Py]、[0313:3−CF3−6−Me−2−Py]、[0314:4−CF3−6−Me−2−Py]、[0315:5−CF3−6−Me−2−Py]、[0316:3−CN−6−Me−2−Py]、[0317:4−CN−6−Me−2−Py]、[0318:5−CN−6−Me−2−Py]、[0319:3−OMe−6−Me−2−Py]、[0320:4−OMe−6−Me−2−Py]、[0321:5−OMe−6−Me−2−Py]、[0322:3−OMe−2−Py]、[0323:4−Cl−3−OMe−2−Py]、[0324:5−Cl−3−OMe−2−Py]、[0325:6−Cl−3−OMe−2−Py]、[0326:4−Me−3−OMe−2−Py]、[0327:5−Me−3−OMe−2−Py]、[0328:6−Me−3−OMe−2−Py]、[0329:4−CF3−3−OMe−2−Py]、[0330:5−CF3−3−OMe−2−Py]、[0331:6−CF3−3−OMe−2−Py]、[0332:4−CN−3−OMe−2−Py]、[0333:5−CN−3−OMe−2−Py]、[0334:6−CN−3−OMe−2−Py]、[0335:4−OMe−3−OMe−2−Py]、[0336:5−OMe−3−OMe−2−Py]、[0337:6−OMe−3−OMe−2−Py]、[0338:4−OMe−2−Py]、[0339:3−Cl−4−OMe−2−Py]、[0340:5−Cl−4−OMe−2−Py]、[0341:6−Cl−4−OMe−2−Py]、[0342:3−Me−4−OMe−2−Py]、[0343:5−Me−4−OMe−2−Py]、[0344:6−Me−4−OMe−2−Py]、[0345:3−CF3−4−OMe−2−Py]、[0346:5−CF3−4−OMe−2−Py]、[0347:6−CF3−4−OMe−2−Py]、[0348:3−CN−4−OMe−2−Py]、[0349:5−CN−4−OMe−2−Py]、[0350:6−CN−4−OMe−2−Py]、[0351:3−OMe−4−OMe−2−Py]、[0352:5−OMe−4−OMe−2−Py]、[0353:6−OMe−4−OMe−2−Py]、[0354:5−OMe−2−Py]、[0355:3−Cl−5−OMe−2−Py]、[0356:4−Cl−5−OMe−2−Py]、[0357:6−Cl−5−OMe−2−Py]、[0358:3−Me−5−OMe−2−Py]、[0359:4−Me−5−OMe−2−Py]、[0360:6−Me−5−OMe−2−Py]、[0361:3−CF3−5−OMe−2−Py]、[0362:4−CF3−5−OMe−2−Py]、[0363:6−CF3−5−OMe−2−Py]、[0364:3−CN−5−OMe−2−Py]、[0365:4−CN−5−OMe−2−Py]、[0366:6−CN−5−OMe−2−Py]、[0367:3−OMe−5−OMe−2−Py]、[0368:4−OMe−5−OMe−2−Py]、[0369:6−OMe−5−OMe−2−Py]、[0370:6−OMe−2−Py]、[0371:3−Cl−6−OMe−2−Py]、[0372:4−Cl−6−OMe−2−Py]、[0373:5−Cl−6−OMe−2−Py]、[0374:3−Me−6−OMe−2−Py]、[0375:4−Me−6−OMe−2−Py]、[0376:5−Me−6−OMe−2−Py]、[0377:3−CF3−6−OMe−2−Py]、[0378:4−CF3−6−OMe−2−Py]、[0379:5−CF3−6−OMe−2−Py]、[0380:3−CN−6−OMe−2−Py]、[0381:4−CN−6−OMe−2−Py]、[0382:5−CN−6−OMe−2−Py]、[0383:3−OMe−6−OMe−2−Py]、[0384:4−OMe−6−OMe−2−Py]、[0385:5−OMe−6−OMe−2−Py]、[0386:3−CF3−2−Py]、[0387:4−Cl−3−CF3−2−Py]、[0388:5−Cl−3−CF3−2−Py]、[0389:6−Cl−3−CF3−2−Py]、[0390:4−Me−3−CF3−2−Py]、[0391:5−Me−3−CF3−2−Py]、[0392:6−Me−3−CF3−2−Py]、[0393:4−CF3−3−CF3−2−Py]、[0394:5−CF3−3−CF3−2−Py]、[0395:6−CF3−3−CF3−2−Py]、[0396:4−CN−3−CF3−2−Py]、[0397:5−CN−3−CF3−2−Py]、[0398:6−CN−3−CF3−2−Py]、[0399:4−OMe−3−CF3−2−Py]、[0400:5−OMe−3−CF3−2−Py]、 [0301: 4-CN-5-Me-2-Py], [0302: 6-CN-5-Me-2-Py], [0303: 3-OMe-5-Me-2-Py], [0304 : 4-OMe-5-Me-2-Py], [0305: 6-OMe-5-Me-2-Py], [0306: 6-Me-2-Py], [0307: 3-Cl-6 -Me-2-Py], [0308: 4-Cl-6-Me-2-Py], [0309: 5-Cl-6-Me-2-Py], [0310: 3-Me-6-Me -2-Py], [0311: 4-Me-6-Me-2-Py], [0312: 5-Me-6-Me-2-Py], [0313: 3-CF3-6-Me-2 -Py], [0314: 4-CF3-6-Me-2-Py], [0315: 5-CF3-6-Me-2-Py], [0 16: 3-CN-6-Me-2-Py], [0317: 4-CN-6-Me-2-Py], [0318: 5-CN-6-Me-2-Py], [0319: 3-OMe-6-Me-2-Py], [0320: 4-OMe-6-Me-2-Py], [0321: 5-OMe-6-Me-2-Py], [0322: 3- OMe-2-Py], [0323: 4-Cl-3-OMe-2-Py], [0324: 5-Cl-3-OMe-2-Py], [0325: 6-Cl-3-OMe- 2-Py], [0326: 4-Me-3-OMe-2-Py], [0327: 5-Me-3-OMe-2-Py], [0328: 6-Me-3-OMe-2- Py], [0329: 4-CF3-3-OMe-2-Py], [0330: 5-CF3-3-OMe-2- y], [0331: 6-CF3-3-OMe-2-Py], [0332: 4-CN-3-OMe-2-Py], [0333: 5-CN-3-OMe-2-Py] [0334: 6-CN-3-OMe-2-Py], [0335: 4-OMe-3-OMe-2-Py], [0336: 5-OMe-3-OMe-2-Py], [ 0337: 6-OMe-3-OMe-2-Py], [0338: 4-OMe-2-Py], [0339: 3-Cl-4-OMe-2-Py], [0340: 5-Cl- 4-OMe-2-Py], [0341: 6-Cl-4-OMe-2-Py], [0342: 3-Me-4-OMe-2-Py], [0343: 5-Me-4- OMe-2-Py], [0344: 6-Me-4-OMe-2-Py], [0345: 3-C F3-4-OMe-2-Py], [0346: 5-CF3-4-OMe-2-Py], [0347: 6-CF3-4-OMe-2-Py], [0348: 3-CN- 4-OMe-2-Py], [0349: 5-CN-4-OMe-2-Py], [0350: 6-CN-4-OMe-2-Py], [0351: 3-OMe-4- OMe-2-Py], [0352: 5-OMe-4-OMe-2-Py], [0353: 6-OMe-4-OMe-2-Py], [0354: 5-OMe-2-Py] [0355: 3-Cl-5-OMe-2-Py], [0356: 4-Cl-5-OMe-2-Py], [0357: 6-Cl-5-OMe-2-Py], [ 0358: 3-Me-5-OMe-2-Py], [0359: 4-Me-5-OMe-2- y], [0360: 6-Me-5-OMe-2-Py], [0361: 3-CF3-5-OMe-2-Py], [0362: 4-CF3-5-OMe-2-Py] [0363: 6-CF3-5-OMe-2-Py], [0364: 3-CN-5-OMe-2-Py], [0365: 4-CN-5-OMe-2-Py], [ 0366: 6-CN-5-OMe-2-Py], [0367: 3-OMe-5-OMe-2-Py], [0368: 4-OMe-5-OMe-2-Py], [0369: 6-OMe-5-OMe-2-Py], [0370: 6-OMe-2-Py], [0371: 3-Cl-6-OMe-2-Py], [0372: 4-Cl-6 OMe-2-Py], [0373: 5-Cl-6-OMe-2-Py], [0374: -Me-6-OMe-2-Py], [0375: 4-Me-6-OMe-2-Py], [0376: 5-Me-6-OMe-2-Py], [0377: 3-CF3 -6-OMe-2-Py], [0378: 4-CF3-6-OMe-2-Py], [0379: 5-CF3-6-OMe-2-Py], [0380: 3-CN-6 -OMe-2-Py], [0391: 4-CN-6-OMe-2-Py], [0382: 5-CN-6-OMe-2-Py], [0383: 3-OMe-6-OMe -2-Py], [0384: 4-OMe-6-OMe-2-Py], [0385: 5-OMe-6-OMe-2-Py], [0386: 3-CF3-2-Py], [0387: 4-Cl-3-CF3-2-Py], [0388: 5-Cl-3-CF3- 2-Py], [0389: 6-Cl-3-CF3-2-Py], [0390: 4-Me-3-CF3-2-Py], [0391: 5-Me-3-CF3-2- Py], [0392: 6-Me-3-CF3-2-Py], [0393: 4-CF3-3-CF3-2-Py], [0394: 5-CF3-3-CF3-2-Py] [0395: 6-CF3-3-CF3-2-Py], [0396: 4-CN-3-CF3-2-Py], [0397: 5-CN-3-CF3-2-Py], [ 0398: 6-CN-3-CF3-2-Py], [0399: 4-OMe-3-CF3-2-Py], [0400: 5-OMe-3-CF3-2-Py],
[0401:6−OMe−3−CF3−2−Py]、[0402:4−CF3−2−Py]、[0403:3−Cl−4−CF3−2−Py]、[0404:5−Cl−4−CF3−2−Py]、[0405:6−Cl−4−CF3−2−Py]、[0406:3−Me−4−CF3−2−Py]、[0407:5−Me−4−CF3−2−Py]、[0408:6−Me−4−CF3−2−Py]、[0409:3−CF3−4−CF3−2−Py]、[0410:5−CF3−4−CF3−2−Py]、[0411:6−CF3−4−CF3−2−Py]、[0412:3−CN−4−CF3−2−Py]、[0413:5−CN−4−CF3−2−Py]、[0414:6−CN−4−CF3−2−Py]、[0415:3−OMe−4−CF3−2−Py]、[0416:5−OMe−4−CF3−2−Py]、[0417:6−OMe−4−CF3−2−Py]、[0418:5−CF3−2−Py]、[0419:3−Cl−5−CF3−2−Py]、[0420:4−Cl−5−CF3−2−Py]、[0421:6−Cl−5−CF3−2−Py]、[0422:3−Me−5−CF3−2−Py]、[0423:4−Me−5−CF3−2−Py]、[0424:6−Me−5−CF3−2−Py]、[0425:3−CF3−5−CF3−2−Py]、[0426:4−CF3−5−CF3−2−Py]、[0427:6−CF3−5−CF3−2−Py]、[0428:3−CN−5−CF3−2−Py]、[0429:4−CN−5−CF3−2−Py]、[0430:6−CN−5−CF3−2−Py]、[0431:3−OMe−5−CF3−2−Py]、[0432:4−OMe−5−CF3−2−Py]、[0433:6−OMe−5−CF3−2−Py]、[0434:6−CF3−2−Py]、[0435:3−Cl−6−CF3−2−Py]、[0436:4−Cl−6−CF3−2−Py]、[0437:5−Cl−6−CF3−2−Py]、[0438:3−Me−6−CF3−2−Py]、[0439:4−Me−6−CF3−2−Py]、[0440:5−Me−6−CF3−2−Py]、[0441:3−CF3−6−CF3−2−Py]、[0442:4−CF3−6−CF3−2−Py]、[0443:5−CF3−6−CF3−2−Py]、[0444:3−CN−6−CF3−2−Py]、[0445:4−CN−6−CF3−2−Py]、[0446:5−CN−6−CF3−2−Py]、[0447:3−OMe−6−CF3−2−Py]、[0448:4−OMe−6−CF3−2−Py]、[0449:5−OMe−6−CF3−2−Py]、[0450:3−OCF3−2−Py]、[0451:4−Cl−3−OCF3−2−Py]、[0452:5−Cl−3−OCF3−2−Py]、[0453:6−Cl−3−OCF3−2−Py]、[0454:4−Me−3−OCF3−2−Py]、[0455:5−Me−3−OCF3−2−Py]、[0456:6−Me−3−OCF3−2−Py]、[0457:4−CF3−3−OCF3−2−Py]、[0458:5−CF3−3−OCF3−2−Py]、[0459:6−CF3−3−OCF3−2−Py]、[0460:4−CN−3−OCF3−2−Py]、[0461:5−CN−3−OCF3−2−Py]、[0462:6−CN−3−OCF3−2−Py]、[0463:4−OMe−3−OCF3−2−Py]、[0464:5−OMe−3−OCF3−2−Py]、[0465:6−OMe−3−OCF3−2−Py]、[0466:4−OCF3−2−Py]、[0467:3−Cl−4−OCF3−2−Py]、[0468:5−Cl−4−OCF3−2−Py]、[0469:6−Cl−4−OCF3−2−Py]、[0470:3−Me−4−OCF3−2−Py]、[0471:5−Me−4−OCF3−2−Py]、[0472:6−Me−4−OCF3−2−Py]、[0473:3−CF3−4−OCF3−2−Py]、[0474:5−CF3−4−OCF3−2−Py]、[0475:6−CF3−4−OCF3−2−Py]、[0476:3−CN−4−OCF3−2−Py]、[0477:5−CN−4−OCF3−2−Py]、[0478:6−CN−4−OCF3−2−Py]、[0479:3−OMe−4−OCF3−2−Py]、[0480:5−OMe−4−OCF3−2−Py]、[0481:6−OMe−4−OCF3−2−Py]、[0482:5−OCF3−2−Py]、[0483:3−Cl−5−OCF3−2−Py]、[0484:4−Cl−5−OCF3−2−Py]、[0485:6−Cl−5−OCF3−2−Py]、[0486:3−Me−5−OCF3−2−Py]、[0487:4−Me−5−OCF3−2−Py]、[0488:6−Me−5−OCF3−2−Py]、[0489:3−CF3−5−OCF3−2−Py]、[0490:4−CF3−5−OCF3−2−Py]、[0491:6−CF3−5−OCF3−2−Py]、[0492:3−CN−5−OCF3−2−Py]、[0493:4−CN−5−OCF3−2−Py]、[0494:6−CN−5−OCF3−2−Py]、[0495:3−OMe−5−OCF3−2−Py]、[0496:4−OMe−5−OCF3−2−Py]、[0497:6−OMe−5−OCF3−2−Py]、[0498:6−OCF3−2−Py]、[0499:3−Cl−6−OCF3−2−Py]、[0500:4−Cl−6−OCF3−2−Py]、 [0401: 6-OMe-3-CF3-2-Py], [0402: 4-CF3-2-Py], [0403: 3-Cl-4-CF3-2-Py], [0404: 5-Cl -4-CF3-2-Py], [0405: 6-Cl-4-CF3-2-Py], [0406: 3-Me-4-CF3-2-Py], [0407: 5-Me-4 -CF3-2-Py], [0408: 6-Me-4-CF3-2-Py], [0409: 3-CF3-4-CF3-2-Py], [0410: 5-CF3-4-CF3 -2-Py], [0411: 6-CF3-4-CF3-2-Py], [0412: 3-CN-4-CF3-2-Py], [0413: 5-CN-4-CF3-2 -Py], [0414: 6-CN-4-CF3-2-Py], [0415: 3-OMe- -CF3-2-Py], [0416: 5-OMe-4-CF3-2-Py], [0417: 6-OMe-4-CF3-2-Py], [0418: 5-CF3-2-Py] ], [0419: 3-Cl-5-CF3-2-Py], [0420: 4-Cl-5-CF3-2-Py], [0421: 6-Cl-5-CF3-2-Py], [0422: 3-Me-5-CF3-2-Py], [0423: 4-Me-5-CF3-2-Py], [0424: 6-Me-5-CF3-2-Py], [0425] : 3-CF3-5-CF3-2-Py], [0426: 4-CF3-5-CF3-2-Py], [0427: 6-CF3-5-CF3-2-Py], [0428: 3 -CN-5-CF3-2-Py], [0429: 4-CN-5-CF3-2-Py] [0430: 6-CN-5-CF3-2-Py], [0431: 3-OMe-5-CF3-2-Py], [0432: 4-OMe-5-CF3-2-Py], [0433 : 6-OMe-5-CF3-2-Py], [0434: 6-CF3-2-Py], [0435: 3-Cl-6-CF3-2-Py], [0436: 4-Cl-6 -CF3-2-Py], [0437: 5-Cl-6-CF3-2-Py], [0438: 3-Me-6-CF3-2-Py], [0439: 4-Me-6-CF3 -2-Py], [0440: 5-Me-6-CF3-2-Py], [0441: 3-CF3-6-CF3-2-Py], [0442: 4-CF3-6-CF3-2 -Py], [0443: 5-CF3-6-CF3-2-Py], [0444: 3-CN. -6-CF3-2-Py], [0445: 4-CN-6-CF3-2-Py], [0446: 5-CN-6-CF3-2-Py], [0447: 3-OMe-6. -CF3-2-Py], [0448: 4-OMe-6-CF3-2-Py], [0449: 5-OMe-6-CF3-2-Py], [0450: 3-OCF3-2-Py ], [0451: 4-Cl-3-OCF3-2-Py], [0452: 5-Cl-3-OCF3-2-Py], [0453: 6-Cl-3-OCF3-2-Py], [0454: 4-Me-3-OCF3-2-Py], [0455: 5-Me-3-OCF3-2-Py], [0456: 6-Me-3-OCF3-2-Py], [0457] : 4-CF3-3-OCF3-2-Py], [0458: 5-CF3-3- CF3-2-Py], [0459: 6-CF3-3-OCF3-2-Py], [0460: 4-CN-3-OCF3-2-Py], [0461: 5-CN-3-OCF3- 2-Py], [0462: 6-CN-3-OCF3-2-Py], [0463: 4-OMe-3-OCF3-2-Py], [0464: 5-OMe-3-OCF3-2- Py], [0465: 6-OMe-3-OCF3-2-Py], [0466: 4-OCF3-2-Py], [0467: 3-Cl-4-OCF3-2-Py], [0468: 5-Cl-4-OCF3-2-Py], [0469: 6-Cl-4-OCF3-2-Py], [0470: 3-Me-4-OCF3-2-Py], [0471: 5- Me-4-OCF3-2-Py], [0472: 6-Me- -OCF3-2-Py], [0473: 3-CF3-4-OCF3-2-Py], [0474: 5-CF3-4-OCF3-2-Py], [0475: 6-CF3-4-OCF3 -2-Py], [0476: 3-CN-4-OCF3-2-Py], [0477: 5-CN-4-OCF3-2-Py], [0478: 6-CN-4-OCF3-2 -Py], [0479: 3-OMe-4-OCF3-2-Py], [0480: 5-OMe-4-OCF3-2-Py], [0481: 6-OMe-4-OCF3-2-Py ], [0482: 5-OCF3-2-Py], [0483: 3-Cl-5-OCF3-2-Py], [0484: 4-Cl-5-OCF3-2-Py], [0485: 6 -Cl-5-OCF3-2-Py], [0486: 3- Me-5-OCF3-2-Py], [0487: 4-Me-5-OCF3-2-Py], [0488: 6-Me-5-OCF3-2-Py], [0489: 3-CF3- 5-OCF3-2-Py], [0490: 4-CF3-5-OCF3-2-Py], [0491: 6-CF3-5-OCF3-2-Py], [0492: 3-CN-5 OCF3-2-Py], [0493: 4-CN-5-OCF3-2-Py], [0494: 6-CN-5-OCF3-2-Py], [0495: 3-OMe-5-OCF3- 2-Py], [0496: 4-OMe-5-OCF3-2-Py], [0497: 6-OMe-5-OCF3-2-Py], [0498: 6-OCF3-2-Py], [ 0499: 3-Cl-6-OCF3-2-Py], [050 : 4-Cl-6-OCF3-2-Py],
[0501:5−Cl−6−OCF3−2−Py]、[0502:3−Me−6−OCF3−2−Py]、[0503:4−Me−6−OCF3−2−Py]、[0504:5−Me−6−OCF3−2−Py]、[0505:3−CF3−6−OCF3−2−Py]、[0506:4−CF3−6−OCF3−2−Py]、[0507:5−CF3−6−OCF3−2−Py]、[0508:3−CN−6−OCF3−2−Py]、[0509:4−CN−6−OCF3−2−Py]、[0510:5−CN−6−OCF3−2−Py]、[0511:3−OMe−6−OCF3−2−Py]、[0512:4−OMe−6−OCF3−2−Py]、[0513:5−OMe−6−OCF3−2−Py]、[0514:3−CHF2−2−Py]、[0515:4−Cl−3−CHF2−2−Py]、[0516:5−Cl−3−CHF2−2−Py]、[0517:6−Cl−3−CHF2−2−Py]、[0518:4−Me−3−CHF2−2−Py]、[0519:5−Me−3−CHF2−2−Py]、[0520:6−Me−3−CHF2−2−Py]、[0521:4−CF3−3−CHF2−2−Py]、[0522:5−CF3−3−CHF2−2−Py]、[0523:6−CF3−3−CHF2−2−Py]、[0524:4−CN−3−CHF2−2−Py]、[0525:5−CN−3−CHF2−2−Py]、[0526:6−CN−3−CHF2−2−Py]、[0527:4−OMe−3−CHF2−2−Py]、[0528:5−OMe−3−CHF2−2−Py]、[0529:6−OMe−3−CHF2−2−Py]、[0530:4−CHF2−2−Py]、[0531:3−Cl−4−CHF2−2−Py]、[0532:5−Cl−4−CHF2−2−Py]、[0533:6−Cl−4−CHF2−2−Py]、[0534:3−Me−4−CHF2−2−Py]、[0535:5−Me−4−CHF2−2−Py]、[0536:6−Me−4−CHF2−2−Py]、[0537:3−CF3−4−CHF2−2−Py]、[0538:5−CF3−4−CHF2−2−Py]、[0539:6−CF3−4−CHF2−2−Py]、[0540:3−CN−4−CHF2−2−Py]、[0541:5−CN−4−CHF2−2−Py]、[0542:6−CN−4−CHF2−2−Py]、[0543:3−OMe−4−CHF2−2−Py]、[0544:5−OMe−4−CHF2−2−Py]、[0545:6−OMe−4−CHF2−2−Py]、[0546:5−CHF2−2−Py]、[0547:3−Cl−5−CHF2−2−Py]、[0548:4−Cl−5−CHF2−2−Py]、[0549:6−Cl−5−CHF2−2−Py]、[0550:3−Me−5−CHF2−2−Py]、[0551:4−Me−5−CHF2−2−Py]、[0552:6−Me−5−CHF2−2−Py]、[0553:3−CF3−5−CHF2−2−Py]、[0554:4−CF3−5−CHF2−2−Py]、[0555:6−CF3−5−CHF2−2−Py]、[0556:3−CN−5−CHF2−2−Py]、[0557:4−CN−5−CHF2−2−Py]、[0558:6−CN−5−CHF2−2−Py]、[0559:3−OMe−5−CHF2−2−Py]、[0560:4−OMe−5−CHF2−2−Py]、[0561:6−OMe−5−CHF2−2−Py]、[0562:6−CHF2−2−Py]、[0563:3−Cl−6−CHF2−2−Py]、[0564:4−Cl−6−CHF2−2−Py]、[0565:5−Cl−6−CHF2−2−Py]、[0566:3−Me−6−CHF2−2−Py]、[0567:4−Me−6−CHF2−2−Py]、[0568:5−Me−6−CHF2−2−Py]、[0569:3−CF3−6−CHF2−2−Py]、[0570:4−CF3−6−CHF2−2−Py]、[0571:5−CF3−6−CHF2−2−Py]、[0572:3−CN−6−CHF2−2−Py]、[0573:4−CN−6−CHF2−2−Py]、[0574:5−CN−6−CHF2−2−Py]、[0575:3−OMe−6−CHF2−2−Py]、[0576:4−OMe−6−CHF2−2−Py]、[0577:5−OMe−6−CHF2−2−Py]、[0578:3−OCHF2−2−Py]、[0579:4−Cl−3−OCHF2−2−Py]、[0580:5−Cl−3−OCHF2−2−Py]、[0581:6−Cl−3−OCHF2−2−Py]、[0582:4−Me−3−OCHF2−2−Py]、[0583:5−Me−3−OCHF2−2−Py]、[0584:6−Me−3−OCHF2−2−Py]、[0585:4−CF3−3−OCHF2−2−Py]、[0586:5−CF3−3−OCHF2−2−Py]、[0587:6−CF3−3−OCHF2−2−Py]、[0588:4−CN−3−OCHF2−2−Py]、[0589:5−CN−3−OCHF2−2−Py]、[0590:6−CN−3−OCHF2−2−Py]、[0591:4−OMe−3−OCHF2−2−Py]、[0592:5−OMe−3−OCHF2−2−Py]、[0593:6−OMe−3−OCHF2−2−Py]、[0594:4−OCHF2−2−Py]、[0595:3−Cl−4−OCHF2−2−Py]、[0596:5−Cl−4−OCHF2−2−Py]、[0597:6−Cl−4−OCHF2−2−Py]、[0598:3−Me−4−OCHF2−2−Py]、[0599:5−Me−4−OCHF2−2−Py]、[0600:6−Me−4−OCHF2−2−Py]、 [0501: 5-Cl-6-OCF3-2-Py], [0502: 3-Me-6-OCF3-2-Py], [0503: 4-Me-6-OCF3-2-Py], [0504] : 5-Me-6-OCF3-2-Py], [0505: 3-CF3-6-OCF3-2-Py], [0506: 4-CF3-6-OCF3-2-Py], [0507: 5 -CF3-6-OCF3-2-Py], [0508: 3-CN-6-OCF3-2-Py], [0509: 4-CN-6-OCF3-2-Py], [0510: 5-CN -6-OCF3-2-Py], [0511: 3-OMe-6-OCF3-2-Py], [0512: 4-OMe-6-OCF3-2-Py], [0513: 5-OMe-6. -OCF3-2-Py], [0514: 3-CHF2-2 y], [0515: 4-Cl-3-CHF2-2-Py], [0516: 5-Cl-3-CHF2-2-Py], [0517: 6-Cl-3-CHF2-2-Py] [0518: 4-Me-3-CHF2-2Py], [0519: 5-Me-3-CHF2-2Py], [0520: 6-Me-3-CHF2-2Py], [ 0521: 4-CF3-3-CHF2-2Py], [0522: 5-CF3-3-CHF2-2Py], [0523: 6-CF3-3-CHF2-2Py], [0524: 4-CN-3-CHF2-2-Py], [0525: 5-CN-3-CHF2-2-Py], [0526: 6-CN-3-CHF2-2-Py], [0527: 4- OMe-3-CHF2-2Py], [0528: 5-OMe-3 CHF2-2-Py], [0529: 6-OMe-3-CHF2-2-Py], [0530: 4-CHF2-2-Py], [0531: 3-Cl-4-CHF2-2-Py] [0532: 5-Cl-4-CHF2-2-Py], [0533: 6-Cl-4-CHF2-2-Py], [0534: 3-Me-4-CHF2-2-Py], [ 0535: 5-Me-4-CHF2-2Py], [0536: 6-Me-4-CHF2-2Py], [0537: 3-CF3-4-CHF2-2Py], [0538: 5-CF3-4-CHF2-2Py], [0539: 6-CF3-4-CHF2-2Py], [0540: 3-CN-4-CHF2-2Py], [0541: 5- CN-4-CHF2-2-Py], [0542: 6-CN- 4-CHF2-2-Py], [0543: 3-OMe-4-CHF2-2-Py], [0544: 5-OMe-4-CHF2-2-Py], [0545: 6-OMe-4- CHF2-2-Py], [0546: 5-CHF2-2-Py], [0547: 3-Cl-5-CHF2-2-Py], [0548: 4-Cl-5-CHF2-2-Py] [0549: 6-Cl-5-CHF2-2Py], [0550: 3-Me-5-CHF2-2Py], [0551: 4-Me-5-CHF2-2Py], [ 0552: 6-Me-5-CHF2-2Py], [0553: 3-CF3-5-CHF2-2Py], [0554: 4-CF3-5-CHF2-2Py], [0555: 6-CF3-5-CHF2-2Py], [0556: 3 CN-5-CHF2-2-Py], [0557: 4-CN-5-CHF2-2-Py], [0558: 6-CN-5-CHF2-2-Py], [0559: 3-OMe- 5-CHF2-2-Py], [0560: 4-OMe-5-CHF2-2-Py], [0561: 6-OMe-5-CHF2-2-Py], [0562: 6-CHF2-2 Py], [0563: 3-Cl-6-CHF2-2-Py], [0564: 4-Cl-6-CHF2-2-Py], [0565: 5-Cl-6-CHF2-2-Py] [0566: 3-Me-6-CHF2-2Py], [0567: 4-Me-6-CHF2-2Py], [0568: 5-Me-6-CHF2-2Py], [ 0568: 3-CF3-6-CHF2-2Py], [0570 4-CF3-6-CHF2-2Py], [0571: 5-CF3-6-CHF2-2Py], [0572: 3-CN-6-CHF2-2Py], [0573: 4- CN-6-CHF2-2-Py], [0574: 5-CN-6-CHF2-2-Py], [0575: 3-OMe-6-CHF2-2-Py], [0576: 4-OMe- 6-CHF2-2-Py], [0577: 5-OMe-6-CHF2-2-Py], [0578: 3-OCHF2-2-Py], [0579: 4-Cl-3-OCHF2-2 Py], [0580: 5-Cl-3-OCHF2-2-Py], [0581: 6-Cl-3-OCHF2-2-Py], [0582: 4-Me-3-OCHF2-2-Py] [0583: 5-Me-3-OCHF2-2-P y], [0584: 6-Me-3-OCHF2-2-Py], [0585: 4-CF3-3-OCHF2-2-Py], [0586: 5-CF3-3-OCHF2-2-Py] [0587: 6-CF3-3-OCHF2-2-Py], [0588: 4-CN-3-OCHF2-2-Py], [0589: 5-CN-3-OCHF2-2-Py], [ 0590: 6-CN-3-OCHF2-2-Py], [0591: 4-OMe-3-OCHF2-2-Py], [0592: 5-OMe-3-OCHF2-2-Py], [0593: 6-OMe-3-OCHF2-2-Py], [0594: 4-OCHF2-2-Py], [0595: 3-Cl-4-OCHF2-2-Py], [0596: 5-Cl-4- OCHF2-2-Py], [059 : 6-Cl-4-OCHF2-2-Py], [0598: 3-Me-4-OCHF2-2-Py], [0599: 5-Me-4-OCHF2-2-Py], [0600: 6 -Me-4-OCHF2-2-Py],
[0601:3−CF3−4−OCHF2−2−Py]、[0602:5−CF3−4−OCHF2−2−Py]、[0603:6−CF3−4−OCHF2−2−Py]、[0604:3−CN−4−OCHF2−2−Py]、[0605:5−CN−4−OCHF2−2−Py]、[0606:6−CN−4−OCHF2−2−Py]、[0607:3−OMe−4−OCHF2−2−Py]、[0608:5−OMe−4−OCHF2−2−Py]、[0609:6−OMe−4−OCHF2−2−Py]、[0610:5−OCHF2−2−Py]、[0611:3−Cl−5−OCHF2−2−Py]、[0612:4−Cl−5−OCHF2−2−Py]、[0613:6−Cl−5−OCHF2−2−Py]、[0614:3−Me−5−OCHF2−2−Py]、[0615:4−Me−5−OCHF2−2−Py]、[0616:6−Me−5−OCHF2−2−Py]、[0617:3−CF3−5−OCHF2−2−Py]、[0618:4−CF3−5−OCHF2−2−Py]、[0619:6−CF3−5−OCHF2−2−Py]、[0620:3−CN−5−OCHF2−2−Py]、[0621:4−CN−5−OCHF2−2−Py]、[0622:6−CN−5−OCHF2−2−Py]、[0623:3−OMe−5−OCHF2−2−Py]、[0624:4−OMe−5−OCHF2−2−Py]、[0625:6−OMe−5−OCHF2−2−Py]、[0626:6−OCHF2−2−Py]、[0627:3−Cl−6−OCHF2−2−Py]、[0628:4−Cl−6−OCHF2−2−Py]、[0629:5−Cl−6−OCHF2−2−Py]、[0630:3−Me−6−OCHF2−2−Py]、[0631:4−Me−6−OCHF2−2−Py]、[0632:5−Me−6−OCHF2−2−Py]、[0633:3−CF3−6−OCHF2−2−Py]、[0634:4−CF3−6−OCHF2−2−Py]、[0635:5−CF3−6−OCHF2−2−Py]、[0636:3−CN−6−OCHF2−2−Py]、[0637:4−CN−6−OCHF2−2−Py]、[0638:5−CN−6−OCHF2−2−Py]、[0639:3−OMe−6−OCHF2−2−Py]、[0640:4−OMe−6−OCHF2−2−Py]、[0641:5−OMe−6−OCHP2−2−Py]、[0642:3−Et−2−Py]、[0643:4−Cl−3−Et−2−Py]、[0644:5−Cl−3−Et−2−Py]、[0645:6−Cl−3−Et−2−Py]、[0646:4−Me−3−Et−2−Py]、[0647:5−Me−3−Et−2−Py]、[0648:6−Me−3−Et−2−Py]、[0649:4−CF3−3−Et−2−Py]、[0650:5−CF3−3−Et−2−Py]、[0651:6−CF3−3−Et−2−Py]、[0652:4−CN−3−Et−2−Py]、[0653:5−CN−3−Et−2−Py]、[0654:6−CN−3−Et−2−Py]、[0655:4−OMe−3−Et−2−Py]、[0656:5−OMe−3−Et−2−Py]、[0657:6−OMe−3−Et−2−Py]、[0658:4−Et−2−Py]、[0659:3−Cl−4−Et−2−Py]、[0660:5−Cl−4−Et−2−Py]、[0661:6−Cl−4−Et−2−Py]、[0662:3−Me−4−Et−2−Py]、[0663:5−Me−4−Et−2−Py]、[0664:6−Me−4−Et−2−Py]、[0665:3−CF3−4−Et−2−Py]、[0666:5−CF3−4−Et−2−Py]、[0667:6−CF3−4−Et−2−Py]、[0668:3−CN−4−Et−2−Py]、[0669:5−CN−4−Et−2−Py]、[0670:6−CN−4−Et−2−Py]、[0671:3−OMe−4−Et−2−Py]、[0672:5−OMe−4−Et−2−Py]、[0673:6−OMe−4−Et−2−Py]、[0674:5−Et−2−Py]、[0675:3−Cl−5−Et−2−Py]、[0676:4−Cl−5−Et−2−Py]、[0677:6−Cl−5−Et−2−Py]、[0678:3−Me−5−Et−2−Py]、[0679:4−Me−5−Et−2−Py]、[0680:6−Me−5−Et−2−Py]、[0681:3−CF3−5−Et−2−Py]、[0682:4−CF3−5−Et−2−Py]、[0683:6−CF3−5−Et−2−Py]、[0684:3−CN−5−Et−2−Py]、[0685:4−CN−5−Et−2−Py]、[0686:6−CN−5−Et−2−Py]、[0687:3−OMe−5−Et−2−Py]、[0688:4−OMe−5−Et−2−Py]、[0689:6−OMe−5−Et−2−Py]、[0690:6−Et−2−Py]、[0691:3−Cl−6−Et−2−Py]、[0692:4−Cl−6−Et−2−Py]、[0693:5−Cl−6−Et−2−Py]、[0694:3−Me−6−Et−2−Py]、[0695:4−Me−6−Et−2−Py]、[0696:5−Me−6−Et−2−Py]、[0697:3−CF3−6−Et−2−Py]、[0698:4−CF3−6−Et−2−Py]、[0699:5−CF3−6−Et−2−Py]、[0700:3−CN−6−Et−2−Py]、 [0601: 3-CF3-4-OCHF2-2-Py], [0602: 5-CF3-4-OCHF2-2-Py], [0603: 6-CF3-4-OCHF2-2-Py], [0604] : 3-CN-4-OCHF2-2-Py], [0605: 5-CN-4-OCHF2-2-Py], [0606: 6-CN-4-OCHF2-2-Py], [0607: 3 -OMe-4-OCHF2-2-Py], [0608: 5-OMe-4-OCHF2-2-Py], [0609: 6-OMe-4-OCHF2-2-Py], [0610: 5-OCHF2 -2-Py], [0611: 3-Cl-5-OCHF2-2-Py], [0612: 4-Cl-5-OCHF2-2-Py], [0613: 6-Cl-5-OCHF2-2 -Py], [0614: 3 Me-5-OCHF2-2-Py], [0615: 4-Me-5-OCHF2-2-Py], [0616: 6-Me-5-OCHF2-2-Py], [0617: 3-CF3- 5-OCHF2-2-Py], [0618: 4-CF3-5-OCHF2-2-Py], [0619: 6-CF3-5-OCHF2-2-Py], [0620: 3-CN-5 OCHF2-2-Py], [0621: 4-CN-5-OCHF2-2-Py], [0622: 6-CN-5-OCHF2-2-Py], [0623: 3-OMe-5-OCHF2- 2-Py], [0624: 4-OMe-5-OCHF2-2-Py], [0625: 6-OMe-5-OCHF2-2-Py], [0626: 6-OCHF2-2-Py], [ 0627: 3-Cl-6-O HF2-2-Py], [0628: 4-Cl-6-OCHF2-2-Py], [0629: 5-Cl-6-OCHF2-2-Py], [0630: 3-Me-6-OCHF2- 2-Py], [0631: 4-Me-6-OCHF2-2-Py], [0632: 5-Me-6-OCHF2-2-Py], [0633: 3-CF3-6-OCHF2-2 Py], [0634: 4-CF3-6-OCHF2-2Py], [0635: 5-CF3-6-OCHF2-2Py], [0636: 3-CN-6-OCHF2-2Py] [0637: 4-CN-6-OCHF2-2-Py], [0638: 5-CN-6-OCHF2-2-Py], [0639: 3-OMe-6-OCHF2-2-Py], [ 0640: 4-OMe-6-OCHF2 -2-Py], [0641: 5-OMe-6-OCHP2-2-2-Py], [0642: 3-Et-2-Py], [0643: 4-Cl-3-Et-2-Py], [0644: 5-Cl-3-Et-2-Py], [0645: 6-Cl-3-Et-2-Py], [0646: 4-Me-3-Et-2-Py], [0647] : 5-Me-3-Et-2-Py], [0648: 6-Me-3-Et-2-Py], [0649: 4-CF3-3-Et-2-Py], [0650: 5 -CF3-3-Et-2-Py], [0651: 6-CF3-3-Et-2-Py], [0652: 4-CN-3-Et-2-Py], [0653: 5-CN -3-Et-2-Py], [0654: 6-CN-3-Et-2-Py], [0655: 4-OMe-3-Et 2-Py], [0656: 5-OMe-3-Et-2-Py], [0657: 6-OMe-3-Et-2-Py], [0658: 4-Et-2-Py], [ 0659: 3-Cl-4-Et-2-Py], [0660: 5-Cl-4-Et-2-Py], [0661-6-Cl-4-Et-2-Py], [0662: 3-Me-4-Et-2-Py], [0663: 5-Me-4-Et-2-Py], [0664: 6-Me-4-Et-2-Py], [0665: 3- CF3-4-Et-2-Py], [0666: 5-CF3-4-Et-2-Py], [0667: 6-CF3-4-Et-2-Py], [0668: 3-CN- 4-Et-2-Py], [0669: 5-CN-4-Et-2-Py], [0670: 6-CN-4-Et-2- y], [0671: 3-OMe-4-Et-2-Py], [0672: 5-OMe-4-Et-2-Py], [0673: 6-OMe-4-Et-2-Py] [0674: 5-Et-2-Py], [0675: 3-Cl-5-Et-2-Py], [0676: 4-Cl-5-Et-2-Py], [0677: 6- Cl-5-Et-2-Py], [0678: 3-Me-5-Et-2-Py], [0679: 4-Me-5-Et-2-Py], [0680: 6-Me- 5-Et-2-Py], [0681: 3-CF3-5-Et-2-Py], [0682: 4-CF3-5-Et-2-Py], [0683: 6-CF3-5 Et-2-Py], [0684: 3-CN-5-Et-2-Py], [0685: 4-CN-5-Et-2-Py] [0686: 6-CN-5-Et-2-Py], [0687: 3-OMe-5-Et-2-Py], [0688: 4-OMe-5-Et-2-Py], [ 0689: 6-OMe-5-Et-2-Py], [0690: 6-Et-2-Py], [0691: 3-Cl-6-Et-2-Py], [0692: 4-Cl- 6-Et-2-Py], [0693: 5-Cl-6-Et-2-Py], [0694: 3-Me-6-Et-2-Py], [0695: 4-Me-6- Et-2-Py], [0696: 5-Me-6-Et-2-Py], [0697: 3-CF3-6-Et-2-Py], [0698: 4-CF3-6-Et- 2-Py], [0699: 5-CF3-6-Et-2-Py], [0700: 3-CN-6-Et-2-Py],
[0701:4−CN−6−Et−2−Py]、[0702:5−CN−6−Et−2−Py]、[0703:3−OMe−6−Et−2−Py]、[0704:4−OMe−6−Et−2−Py]、[0705:5−OMe−6−Et−2−Py]、[0706:3−CH2CF3−2−Py]、[0707:4−Cl−3−CH2CF3−2−Py]、[0708:5−Cl−3−CH2CF3−2−Py]、[0709:6−Cl−3−CH2CF3−2−Py]、[0710:4−Me−3−CH2CF3−2−Py]、[0711:5−Me−3−CH2CF3−2−Py]、[0712:6−Me−3−CH2CF3−2−Py]、[0713:4−CF3−3−CH2CF3−2−Py]、[0714:5−CF3−3−CH2CF3−2−Py]、[0715:6−CF3−3−CH2CF3−2−Py]、[0716:4−CN−3−CH2CF3−2−Py]、[0717:5−CN−3−CH2CF3−2−Py]、[0718:6−CN−3−CH2CF3−2−Py]、[0719:4−OMe−3−CH2CF3−2−Py]、[0720:5−OMe−3−CH2CF3−2−Py]、[0721:6−OMe−3−CH2CF3−2−Py]、[0722:4−CH2CF3−2−Py]、[0723:3−Cl−4−CH2CF3−2−Py]、[0724:5−Cl−4−CH2CF3−2−Py]、[0725:6−Cl−4−CH2CF3−2−Py]、[0726:3−Me−4−CH2CF3−2−Py]、[0727:5−Me−4−CH2CF3−2−Py]、[0728:6−Me−4−CH2CF3−2−Py]、[0729:3−CF3−4−CH2CF3−2−Py]、[0730:5−CF3−4−CH2CF3−2−Py]、[0731:6−CF3−4−CH2CF3−2−Py]、[0732:3−CN−4−CH2CF3−2−Py]、[0733:5−CN−4−CH2CF3−2−Py]、[0734:6−CN−4−CH2CF3−2−Py]、[0735:3−OMe−4−CH2CF3−2−Py]、[0736:5−OMe−4−CH2CF3−2−Py]、[0737:6−OMe−4−CH2CF3−2−Py]、[0738:5−CH2CF3−2−Py]、[0739:3−Cl−5−CH2CF3−2−Py]、[0740:4−Cl−5−CH2CF3−2−Py]、[0741:6−Cl−5−CH2CF3−2−Py]、[0742:3−Me−5−CH2CF3−2−Py]、[0743:4−Me−5−CH2CF3−2−Py]、[0744:6−Me−5−CH2CF3−2−Py]、[0745:3−CF3−5−CH2CF3−2−Py]、[0746:4−CF3−5−CH2CF3−2−Py]、[0747:6−CF3−5−CH2CF3−2−Py]、[0748:3−CN−5−CH2CF3−2−Py]、[0749:4−CN−5−CH2CF3−2−Py]、[0750:6−CN−5−CH2CF3−2−Py]、[0751:3−OMe−5−CH2CF3−2−Py]、[0752:4−OMe−5−CH2CF3−2−Py]、[0753:6−OMe−5−CH2CF3−2−Py]、[0754:6−CH2CF3−2−Py]、[0755:3−Cl−6−CH2CF3−2−Py]、[0756:4−Cl−6−CH2CF3−2−Py]、[0757:5−Cl−6−CH2CF3−2−Py]、[0758:3−Me−6−CH2CF3−2−Py]、[0759:4−Me−6−CH2CF3−2−Py]、[0760:5−Me−6−CH2CF3−2−Py]、[0761:3−CF3−6−CH2CF3−2−Py]、[0762:4−CF3−6−CH2CF3−2−Py]、[0763:5−CF3−6−CH2CF3−2−Py]、[0764:3−CN−6−CH2CF3−2−Py]、[0765:4−CN−6−CH2CF3−2−Py]、[0766:5−CN−6−CH2CF3−2−Py]、[0767:3−OMe−6−CH2CF3−2−Py]、[0768:4−OMe−6−CH2CF3−2−Py]、[0769:5−OMe−6−CH2CF3−2−Py]、[0770:3−OEt−2−Py]、[0771:4−Cl−3−OEt−2−Py]、[0772:5−Cl−3−OEt−2−Py]、[0773:6−Cl−3−OEt−2−Py]、[0774:4−Me−3−OEt−2−Py]、[0775:5−Me−3−OEt−2−Py]、[0776:6−Me−3−OEt−2−Py]、[0777:4−CF3−3−OEt−2−Py]、[0778:5−CF3−3−OEt−2−Py]、[0779:6−CF3−3−OEt−2−Py]、[0780:4−CN−3−OEt−2−Py]、[0781:5−CN−3−OEt−2−Py]、[0782:6−CN−3−OEt−2−Py]、[0783:4−OMe−3−OEt−2−Py]、[0784:5−OMe−3−OEt−2−Py]、[0785:6−OMe−3−OEt−2−Py]、[0786:4−OEt−2−Py]、[0787:3−Cl−4−OEt−2−Py]、[0788:5−Cl−4−OEt−2−Py]、[0789:6−Cl−4−OEt−2−Py]、[0790:3−Me−4−OEt−2−Py]、[0791:5−Me−4−OEt−2−Py]、[0792:6−Me−4−OEt−2−Py]、[0793:3−CF3−4−OEt−2−Py]、[0794:5−CF3−4−OEt−2−Py]、[0795:6−CF3−4−OEt−2−Py]、[0796:3−CN−4−OEt−2−Py]、[0797:5−CN−4−OEt−2−Py]、[0798:6−CN−4−OEt−2−Py]、[0799:3−OMe−4−OEt−2−Py]、[0800:5−OMe−4−OEt−2−Py]、 [0701: 4-CN-6-Et-2-Py], [0702: 5-CN-6-Et-2-Py], [0703: 3-OMe-6-Et-2-Py], [0704 : 4-OMe-6-Et-2-Py], [0705: 5-OMe-6-Et-2-Py], [0706: 3-CH2CF3-2-Py], [0707: 4-Cl-3] -CH2CF3-2-Py], [0708: 5-Cl-3-CH2CF3-2-Py], [0709: 6-Cl-3-CH2CF3-2-Py], [0710: 4-Me-3-CH2CF3 -2-Py], [0711: 5-Me-3-CH2CF3-2-Py], [0712: 6-Me-3-CH2CF3-2-Py], [0713: 4-CF3-3-CH2CF3-2 -Py], [0714: 5-CF3-3-CH CF3-2-Py], [0715: 6-CF3-3-CH2CF3-2-Py], [0716: 4-CN-3-CH2CF3-2-Py], [0717: 5-CN-3-CH2CF3- 2-Py], [0718: 6-CN-3-CH2CF3-2-Py], [0719: 4-OMe-3-CH2CF3-2-Py], [0720: 5-OMe-3-CH2CF3-2- Py], [0721: 6-OMe-3-CH2CF3-2-Py], [0722: 4-CH2CF3-2-Py], [0723: 3-Cl-4-CH2CF3-2-Py], [0724: 5-Cl-4-CH2CF3-2-Py], [0725: 6-Cl-4-CH2CF3-2-Py], [0726: 3-Me-4-CH2CF3-2-Py], [0727: 5- Me- -CH2CF3-2-Py], [0728: 6-Me-4-CH2CF3-2-Py], [0729: 3-CF3-4-CH2CF3-2-Py], [0730: 5-CF3-4-CH2CF3 -2Py], [0731: 6-CF3-4-CH2CF3-2-Py], [0732: 3-CN-4-CH2CF3-2-Py], [0733: 5-CN-4-CH2CF3-2 -Py], [0734: 6-CN-4-CH2CF3-2-Py], [0735: 3-OMe-4-CH2CF3-2-Py], [0736: 5-OMe-4-CH2CF3-2-Py ], [0737: 6-OMe-4-CH2CF3-2-Py], [0738: 5-CH2CF3-2-Py], [0739: 3-Cl-5-CH2CF3-2-Py], [0740: 4-Cl-5-CH2CF3-2-Py], [0741: 6-Cl-5-CH2CF3-2-Py], [0742: 3-Me-5-CH2CF3-2-Py], [0743: 4- Me-5-CH2CF3-2-Py], [0744: 6-Me-5-CH2CF3-2-Py], [0745: 3-CF3-5-CH2CF3-2-Py], [0746: 4-CF3- 5-CH2CF3-2-Py], [0747: 6-CF3-5-CH2CF3-2-Py], [0748: 3-CN-5-CH2CF3-2-Py], [0749: 4-CN-5 CH2CF3-2-Py], [0750: 6-CN-5-CH2CF3-2-Py], [0751: 3-OMe-5-CH2CF3-2-Py], [0752: 4-OMe-5-CH2CF3- 2- y], [0753: 6-OMe-5-CH2CF3-2-Py], [0754: 6-CH2CF3-2-Py], [0755: 3-Cl-6-CH2CF3-2-Py], [0756: 4-Cl-6-CH2CF3-2-Py], [0757: 5-Cl-6-CH2CF3-2-Py], [0758: 3-Me-6-CH2CF3-2-Py], [0759: 4- Me-6-CH2CF3-2-Py], [0760: 5-Me-6-CH2CF3-2-Py], [0761: 3-CF3-6-CH2CF3-2-Py], [0762: 4-CF3- 6-CH2CF3-2-Py], [0763: 5-CF3-6-CH2CF3-2-Py], [0764: 3-CN-6-CH2CF3-2-Py], [0765: 4-CN-6 CH2CF -2-Py], [0766: 5-CN-6-CH2CF3-2-Py], [0767: 3-OMe-6-CH2CF3-2-Py], [0768: 4-OMe-6-CH2CF3-2 -Py], [0769: 5-OMe-6-CH2CF3-2-Py], [0770: 3-OEt-2-Py], [0771: 4-Cl-3-OEt-2-Py], [0772]. : 5-Cl-3-OEt-2-Py], [0773: 6-Cl-3-OEt-2-Py], [0774: 4-Me-3-OEt-2-Py], [0775: 5 -Me-3-OEt-2-Py], [0776: 6-Me-3-OEt-2-Py], [0777: 4-CF3-3-OEt-2-Py], [0778: 5-CF3 -3-OEt-2-Py], [0779: 6-CF3-3-O Et-2-Py], [0780: 4-CN-3-OEt-2-Py], [0781: 5-CN-3-OEt-2-Py], [0782: 6-CN-3-OEt- 2-Py], [0783: 4-OMe-3-OEt-2-Py], [0784: 5-OMe-3-OEt-2-Py], [0785: 6-OMe-3-OEt-2- Py], [0786: 4-OEt-2-Py], [0787: 3-Cl-4-OEt-2-Py], [0788: 5-Cl-4-OEt-2-Py], [0789: 6-Cl-4-OEt-2-Py], [0790: 3-Me-4-OEt-2-Py], [0791: 5-Me-4-OEt-2-Py], [0792: 6- Me-4-OEt-2-Py], [0793: 3-CF3-4-OEt-2-Py], [07 4: 5-CF3-4-OEt-2-Py], [0795: 6-CF3-4-OEt-2-Py], [0796: 3-CN-4-OEt-2-Py], [0797: 5-CN-4-OEt-2-Py], [0798: 6-CN-4-OEt-2-Py], [0799: 3-OMe-4-OEt-2-Py], [0800: 5- OMe-4-OEt-2-Py],
[0801:6−OMe−4−OEt−2−Py]、[0802:5−OEt−2−Py]、[0803:3−Cl−5−OEt−2−Py]、[0804:4−Cl−5−OEt−2−Py]、[0805:6−Cl−5−OEt−2−Py]、[0806:3−Me−5−OEt−2−Py]、[0807:4−Me−5−OEt−2−Py]、[0808:6−Me−5−OEt−2−Py]、[0809:3−CF3−5−OEt−2−Py]、[0810:4−CF3−5−OEt−2−Py]、[0811:6−CF3−5−OEt−2−Py]、[0812:3−CN−5−OEt−2−Py]、[0813:4−CN−5−OEt−2−Py]、[0814:6−CN−5−OEt−2−Py]、[0815:3−OMe−5−OEt−2−Py]、[0816:4−OMe−5−OEt−2−Py]、[0817:6−OMe−5−OEt−2−Py]、[0818:6−OEt−2−Py]、[0819:3−Cl−6−OEt−2−Py]、[0820:4−Cl−6−OEt−2−Py]、[0821:5−Cl−6−OEt−2−Py]、[0822:3−Me−6−OEt−2−Py]、[0823:4−Me−6−OEt−2−Py]、[0824:5−Me−6−OEt−2−Py]、[0825:3−CF3−6−OEt−2−Py]、[0826:4−CF3−6−OEt−2−Py]、[0827:5−CF3−6−OEt−2−Py]、[0828:3−CN−6−OEt−2−Py]、[0829:4−CN−6−OEt−2−Py]、[0830:5−CN−6−OEt−2−Py]、[0831:3−OMe−6−OEt−2−Py]、[0832:4−OMe−6−OEt−2−Py]、[0833:5−OMe−6−OEt−2−Py]、[0834:3−OCH2CF3−2−Py]、[0835:4−Cl−3−OCH2CF3−2−Py]、[0836:5−Cl−3−OCH2CF3−2−Py]、[0837:6−Cl−3−OCH2CF3−2−Py]、[0838:4−Me−3−OCH2CF3−2−Py]、[0839:5−Me−3−OCH2CF3−2−Py]、[0840:6−Me−3−OCH2CF3−2−Py]、[0841:4−CF3−3−OCH2CF3−2−Py]、[0842:5−CF3−3−OCH2CF3−2−Py]、[0843:6−CF3−3−OCH2CF3−2−Py]、[0844:4−CN−3−OCH2CF3−2−Py]、[0845:5−CN−3−OCH2CF3−2−Py]、[0846:6−CN−3−OCH2CF3−2−Py]、[0847:4−OMe−3−OCH2CF3−2−Py]、[0848:5−OMe−3−OCH2CF3−2−Py]、[0849:6−OMe−3−OCH2CF3−2−Py]、[0850:4−OCH2CF3−2−Py]、[0851:3−Cl−4−OCH2CF3−2−Py]、[0852:5−Cl−4−OCH2CF3−2−Py]、[0853:6−Cl−4−OCH2CF3−2−Py]、[0854:3−Me−4−OCH2CF3−2−Py]、[0855:5−Me−4−OCH2CF3−2−Py]、[0856:6−Me−4−OCH2CF3−2−Py]、[0857:3−CF3−4−OCH2CF3−2−Py]、[0858:5−CF3−4−OCH2CF3−2−Py]、[0859:6−CF3−4−OCH2CF3−2−Py]、[0860:3−CN−4−OCH2CF3−2−Py]、[0861:5−CN−4−OCH2CF3−2−Py]、[0862:6−CN−4−OCH2CF3−2−Py]、[0863:3−OMe−4−OCH2CF3−2−Py]、[0864:5−OMe−4−OCH2CF3−2−Py]、[0865:6−OMe−4−OCH2CF3−2−Py]、[0866:5−OCH2CF3−2−Py]、[0867:3−Cl−5−OCH2CF3−2−Py]、[0868:4−Cl−5−OCH2CF3−2−Py]、[0869:6−Cl−5−OCH2CF3−2−Py]、[0870:3−Me−5−OCH2CF3−2−Py]、[0871:4−Me−5−OCH2CF3−2−Py]、[0872:6−Me−5−OCH2CF3−2−Py]、[0873:3−CF3−5−OCH2CF3−2−Py]、[0874:4−CF3−5−OCH2CF3−2−Py]、[0875:6−CF3−5−OCH2CF3−2−Py]、[0876:3−CN−5−OCH2CF3−2−Py]、[0877:4−CN−5−OCH2CF3−2−Py]、[0878:6−CN−5−OCH2CF3−2−Py]、[0879:3−OMe−5−OCH2CF3−2−Py]、[0880:4−OMe−5−OCH2CF3−2−Py]、[0881:6−OMe−5−OCH2CF3−2−Py]、[0882:6−OCH2CF3−2−Py]、[0883:3−Cl−6−OCH2CF3−2−Py]、[0884:4−Cl−6−OCH2CF3−2−Py]、[0885:5−Cl−6−OCH2CF3−2−Py]、[0886:3−Me−6−OCH2CF3−2−Py]、[0887:4−Me−6−OCH2CF3−2−Py]、[0888:5−Me−6−OCH2CF3−2−Py]、[0889:3−CF3−6−OCH2CF3−2−Py]、[0890:4−CF3−6−OCH2CF3−2−Py]、[0891:5−CF3−6−OCH2CF3−2−Py]、[0892:3−CN−6−OCH2CF3−2−Py]、[0893:4−CN−6−OCH2CF3−2−Py]、[0894:5−CN−6−OCH2CF3−2−Py]、[0895:3−OMe−6−OCH2CF3−2−Py]、[0896:4−OMe−6−OCH2CF3−2−Py]、[0897:5−OMe−6−OCH2CF3−2−Py]、[0898:3−Pr−2−Py]、[0899:4−Cl−3−Pr−2−Py]、[0900:5−Cl−3−Pr−2−Py]、 [0801: 6-OMe-4-OEt-2-Py], [0802: 5-OEt-2-Py], [0803: 3-Cl-5-OEt-2-Py], [0804: 4-Cl -5-OEt-2-Py], [0805: 6-Cl-5-OEt-2-Py], [0806: 3-Me-5-OEt-2-Py], [0807: 4-Me-5. -OEt-2-Py], [0808: 6-Me-5-OEt-2-Py], [0809: 3-CF3-5-OEt-2-Py], [0810: 4-CF3-5-OEt -2-Py], [0811: 6-CF3-5-OEt-2-Py], [0812: 3-CN-5-OEt-2-Py], [0813: 4-CN-5-OEt-2 -Py], [0814: 6-CN-5-OEt-2-Py], [0815: 3-OMe- -OEt-2-Py], [0816: 4-OMe-5-OEt-2-Py], [0817: 6-OMe-5-OEt-2-Py], [0818: 6-OEt-2-Py] ], [0819: 3-Cl-6-OEt-2-Py], [0820: 4-Cl-6-OEt-2-Py], [0821: 5-Cl-6-OEt-2-Py], [0822: 3-Me-6-OEt-2-Py], [0823: 4-Me-6-OEt-2-Py], [0824: 5-Me-6-OEt-2-Py], [0825 : 3-CF3-6-OEt-2-Py], [0826: 4-CF3-6-OEt-2-Py], [0827: 5-CF3-6-OEt-2-Py], [0828: 3 -CN-6-OEt-2-Py], [0829: 4-CN-6-OEt-2-Py] [0830: 5-CN-6-OEt-2-Py], [0831: 3-OMe-6-OEt-2-Py], [0832: 4-OMe-6-OEt-2-Py], [0833] : 5-OMe-6-OEt-2-Py], [0834: 3-OCH2CF3-2-Py], [0835: 4-Cl-3-OCH2CF3-2-Py], [0836: 5-Cl-3 -OCH2CF3-2-Py], [0837: 6-Cl-3-OCH2CF3-2-Py], [0838: 4-Me-3-OCH2CF3-2-Py], [0839: 5-Me-3-OCH2CF3 -2-Py], [0840: 6-Me-3-OCH2CF3-2-Py], [0841: 4-CF3-3-OCH2CF3-2-Py], [0842: 5-CF3-3-OCH2CF3-2 -Py ], [0843: 6-CF3-3-OCH2CF3-2-Py], [0844: 4-CN-3-OCH2CF3-2-Py], [0845: 5-CN-3-OCH2CF3-2-Py], [0846: 6-CN-3-OCH2CF3-2-Py], [0847: 4-OMe-3-OCH2CF3-2-Py], [0848: 5-OMe-3-OCH2CF3-2-Py], [0849 : 6-OMe-3-OCH2CF3-2-Py], [0850: 4-OCH2CF3-2-Py], [0851: 3-Cl-4-OCH2CF3-2-Py], [0852: 5-Cl-4 -OCH2CF3-2-Py], [0853: 6-Cl-4-OCH2CF3-2-Py], [0854: 3-Me-4-OCH2CF3-2-Py], [0855: 5- e-4-OCH2CF3-2-Py], [0856: 6-Me-4-OCH2CF3-2-Py], [0857: 3-CF3-4-OCH2CF3-2-Py], [0858: 5-CF3- 4-OCH2CF3-2-Py], [0859: 6-CF3-4-OCH2CF3-2-Py], [0860: 3-CN-4-OCH2CF3-2-Py], [0861: 5-CN-4- OCH2CF3-2-Py], [0862: 6-CN-4-OCH2CF3-2-Py], [0863: 3-OMe-4-OCH2CF3-2-Py], [0864: 5-OMe-4-OCH2CF3- 2-Py], [0865: 6-OMe-4-OCH2CF3-2-Py], [0866: 5-OCH2CF3-2-Py], [0867: 3-Cl-5-OCH CF3-2-Py], [0868: 4-Cl-5-OCH2CF3-2-Py], [0869: 6-Cl-5-OCH2CF3-2-Py], [0870: 3-Me-5-OCH2CF3- 2-Py], [0871: 4-Me-5-OCH2CF3-2-Py], [0872: 6-Me-5-OCH2CF3-2-Py], [0873: 3-CF3-5-OCH2CF3-2- Py], [0874: 4-CF3-5-OCH2CF3-2-Py], [0875: 6-CF3-5-OCH2CF3-2-Py], [0876: 3-CN-5-OCH2CF3-2-Py] [0877: 4-CN-5-OCH2CF3-2-Py], [0878: 6-CN-5-OCH2CF3-2-Py], [0879: 3-OMe-5-OCH2CF3-2 -Py], [0880: 4-OMe-5-OCH2CF3-2-Py], [0881: 6-OMe-5-OCH2CF3-2-Py], [0882: 6-OCH2CF3-2-Py], [0883 : 3-Cl-6-OCH2CF3-2-Py], [0884: 4-Cl-6-OCH2CF3-2-Py], [0885: 5-Cl-6-OCH2CF3-2-Py], [0886: 3 -Me-6-OCH2CF3-2-Py], [0887: 4-Me-6-OCH2CF3-2-Py], [0888: 5-Me-6-OCH2CF3-2-Py], [0889: 3-CF3 -6-OCH2CF3-2-Py], [0890: 4-CF3-6-OCH2CF3-2-Py], [0891: 5-CF3-6-OCH2CF3-2-Py], [089] : 3-CN-6-OCH2CF3-2-Py], [0893: 4-CN-6-OCH2CF3-2-Py], [0894: 5-CN-6-OCH2CF3-2-Py], [0895: 3 -OMe-6-OCH2CF3-2-Py], [0896: 4-OMe-6-OCH2CF3-2-Py], [0897: 5-OMe-6-OCH2CF3-2-Py], [0898: 3-Pr -2-Py], [0899: 4-Cl-3-Pr-2-Py], [0900: 5-Cl-3-Pr-2-Py],
[0901:6−Cl−3−Pr−2−Py]、[0902:4−Me−3−Pr−2−Py]、[0903:5−Me−3−Pr−2−Py]、[0904:6−Me−3−Pr−2−Py]、[0905:4−CF3−3−Pr−2−Py]、[0906:5−CF3−3−Pr−2−Py]、[0907:6−CF3−3−Pr−2−Py]、[0908:4−CN−3−Pr−2−Py]、[0909:5−CN−3−Pr−2−Py]、[0910:6−CN−3−Pr−2−Py]、[0911:4−OMe−3−Pr−2−Py]、[0912:5−OMe−3−Pr−2−Py]、[0913:6−OMe−3−Pr−2−Py]、[0914:4−Pr−2−Py]、[0915:3−Cl−4−Pr−2−Py]、[0916:5−Cl−4−Pr−2−Py]、[0917:6−Cl−4−Pr−2−Py]、[0918:3−Me−4−Pr−2−Py]、[0919:5−Me−4−Pr−2−Py]、[0920:6−Me−4−Pr−2−Py]、[0921:3−CF3−4−Pr−2−Py]、[0922:5−CF3−4−Pr−2−Py]、[0923:6−CF3−4−Pr−2−Py]、[0924:3−CN−4−Pr−2−Py]、[0925:5−CN−4−Pr−2−Py]、[0926:6−CN−4−Pr−2−Py]、[0927:3−OMe−4−Pr−2−Py]、[0928:5−OMe−4−Pr−2−Py]、[0929:6−OMe−4−Pr−2−Py]、[0930:5−Pr−2−Py]、[0931:3−Cl−5−Pr−2−Py]、[0932:4−Cl−5−Pr−2−Py]、[0933:6−Cl−5−Pr−2−Py]、[0934:3−Me−5−Pr−2−Py]、[0935:4−Me−5−Pr−2−Py]、[0936:6−Me−5−Pr−2−Py]、[0937:3−CF3−5−Pr−2−Py]、[0938:4−CF3−5−Pr−2−Py]、[0939:6−CF3−5−Pr−2−Py]、[0940:3−CN−5−Pr−2−Py]、[0941:4−CN−5−Pr−2−Py]、[0942:6−CN−5−Pr−2−Py]、[0943:3−OMe−5−Pr−2−Py]、[0944:4−OMe−5−Pr−2−Py]、[0945:6−OMe−5−Pr−2−Py]、[0946:6−Pr−2−Py]、[0947:3−Cl−6−Pr−2−Py]、[0948:4−Cl−6−Pr−2−Py]、[0949:5−Cl−6−Pr−2−Py]、[0950:3−Me−6−Pr−2−Py]、[0951:4−Me−6−Pr−2−Py]、[0952:5−Me−6−Pr−2−Py]、[0953:3−CF3−6−Pr−2−Py]、[0954:4−CF3−6−Pr−2−Py]、[0955:5−CF3−6−Pr−2−Py]、[0956:3−CN−6−Pr−2−Py]、[0957:4−CN−6−Pr−2−Py]、[0958:5−CN−6−Pr−2−Py]、[0959:3−OMe−6−Pr−2−Py]、[0960:4−OMe−6−Pr−2−Py]、[0961:5−OMe−6−Pr−2−Py]、[0962:3−OPr−2−Py]、[0963:4−Cl−3−OPr−2−Py]、[0964:5−Cl−3−OPr−2−Py]、[0965:6−Cl−3−OPr−2−Py]、[0966:4−Me−3−OPr−2−Py]、[0967:5−Me−3−OPr−2−Py]、[0968:6−Me−3−OPr−2−Py]、[0969:4−CF3−3−OPr−2−Py]、[0970:5−CF3−3−OPr−2−Py]、[0971:6−CF3−3−OPr−2−Py]、[0972:4−CN−3−OPr−2−Py]、[0973:5−CN−3−OPr−2−Py]、[0974:6−CN−3−OPr−2−Py]、[0975:4−OMe−3−OPr−2−Py]、[0976:5−OMe−3−OPr−2−Py]、[0977:6−OMe−3−OPr−2−Py]、[0978:4−OPr−2−Py]、[0979:3−Cl−4−OPr−2−Py]、[0980:5−Cl−4−OPr−2−Py]、[0981:6−Cl−4−OPr−2−Py]、[0982:3−Me−4−OPr−2−Py]、[0983:5−Me−4−OPr−2−Py]、[0984:6−Me−4−OPr−2−Py]、[0985:3−CF3−4−OPr−2−Py]、[0986:5−CF3−4−OPr−2−Py]、[0987:6−CF3−4−OPr−2−Py]、[0988:3−CN−4−OPr−2−Py]、[0989:5−CN−4−OPr−2−Py]、[0990:6−CN−4−OPr−2−Py]、[0991:3−OMe−4−OPr−2−Py]、[0992:5−OMe−4−OPr−2−Py]、[0993:6−OMe−4−OPr−2−Py]、[0994:5−OPr−2−Py]、[0995:3−Cl−5−OPr−2−Py]、[0996:4−Cl−5−OPr−2−Py]、[0997:6−Cl−5−OPr−2−Py]、[0998:3−Me−5−OPr−2−Py]、[0999:4−Me−5−OPr−2−Py]、[1000:6−Me−5−OPr−2−Py]、 [0901: 6-Cl-3-Pr-2-Py], [0902: 4-Me-3-Pr-2-Py], [0903: 5-Me-3-Pr-2-Py], [0904] : 6-Me-3-Pr-2-Py], [0905: 4-CF3-3-Pr-2-Py], [0906: 5-CF3-3-Pr-2-Py], [0907: 6 -CF3-3-Pr-2-Py], [0908: 4-CN-3-Pr-2-Py], [0909: 5-CN-3-Pr-2-Py], [0910: 6-CN -3-Pr-2-Py], [0911: 4-OMe-3-Pr-2-Py], [0912: 5-OMe-3-Pr-2-Py], [0913: 6-OMe-3 -Pr-2-Py], [0914: 4-Pr-2-Py], [0915: 3-Cl-4-Pr-2-Py], [0 16: 5-Cl-4-Pr-2-Py], [0917: 6-Cl-4-Pr-2-Py], [0918: 3-Me-4-Pr-2-Py], [0919: 5-Me-4-Pr-2-Py], [0920: 6-Me-4-Pr-2-Py], [0921: 3-CF3-4-Pr-2-Py], [0922: 5- CF3-4-Pr-2-Py], [0923: 6-CF3-4-Pr-2-Py], [0924: 3-CN-4-Pr-2-Py], [0925: 5-CN- 4-Pr-2-Py], [0926: 6-CN-4-Pr-2-Py], [0927: 3-OMe-4-Pr-2-Py], [0928: 5-OMe-4- Pr-2-Py], [0929: 6-OMe-4-Pr-2-Py], [0930: 5-Pr-2-Py], [093 : 3-Cl-5-Pr-2-Py], [0932: 4-Cl-5-Pr-2-Py], [0933: 6-Cl-5-Pr-2-Py], [0934: 3 -Me-5-Pr-2-Py], [0935: 4-Me-5-Pr-2-Py], [0936: 6-Me-5-Pr-2-Py], [0937: 3-CF3 -5-Pr-2-Py], [0938: 4-CF3-5-Pr-2-Py], [0939: 6-CF3-5-Pr-2-Py], [0940: 3-CN-5. -Pr-2-Py], [0941: 4-CN-5-Pr-2-Py], [0942: 6-CN-5-Pr-2-Py], [0943: 3-OMe-5-Pr -2-Py], [0944: 4-OMe-5-Pr-2-Py], [0945: 6-OMe-5-Pr-2-Py], [0 946: 6-Pr-2-Py], [0947: 3-Cl-6-Pr-2-Py], [0948: 4-Cl-6-Pr-2-Py], [0949: 5-Cl- 6-Pr-2-Py], [0950: 3-Me-6-Pr-2-Py], [0951: 4-Me-6-Pr-2-Py], [0952: 5-Me-6-6 Pr-2-Py], [0953: 3-CF3-6-Pr-2-Py], [0954: 4-CF3-6-Pr-2-Py], [0955: 5-CF3-6-Pr- 2-Py], [0956: 3-CN-6-Pr-2-Py], [0957: 4-CN-6-Pr-2-Py], [0958: 5-CN-6-Pr-2- Py], [0959: 3-OMe-6-Pr-2-Py], [0960: 4-OMe-6-Pr-2-Py], [0961 5-OMe-6-Pr-2-Py], [0962: 3-OPr-2-Py], [0963: 4-Cl-3-OPr-2-Py], [0964: 5-Cl-3- OPr-2-Py], [0965: 6-Cl-3-OPr-2-Py], [0966: 4-Me-3-OPr-2-Py], [0967: 5-Me-3-OPr- 2-Py], [0968: 6-Me-3-OPr-2-Py], [0969: 4-CF3-3-OPr-2-Py], [0970: 5-CF3-3-OPr-2- Py], [0971: 6-CF3-3-OPr-2-Py], [0972: 4-CN-3-OPr-2-Py], [0973: 5-CN-3-OPr-2-Py] [0974: 6-CN-3-OPr-2-Py], [0975: 4-OMe-3-OPr- -Py], [0976: 5-OMe-3-OPr-2-Py], [0977: 6-OMe-3-OPr-2-Py], [0978: 4-OPr-2-Py], [0979] : 3-Cl-4-OPr-2-Py], [0980: 5-Cl-4-OPr-2-Py], [0981: 6-Cl-4-OPr-2-Py], [0982: 3 -Me-4-OPr-2-Py], [0983: 5-Me-4-OPr-2-Py], [0984: 6-Me-4-OPr-2-Py], [0985: 3-CF3 -4-OPr-2-Py], [0986: 5-CF3-4-OPr-2-Py], [0987: 6-CF3-4-OPr-2-Py], [0988: 3-CN-4 -OPr-2-Py], [0989: 5-CN-4-OPr-2-Py], [0990: 6-CN-4-OPr-2-Py], [0991: 3-OMe-4-OPr-2-Py], [0992: 5-OMe-4-OPr-2-Py], [0993: 6- OMe-4-OPr-2-Py], [0994: 5-OPr-2-Py], [0995: 3-Cl-5-OPr-2-Py], [0996: 4-Cl-5-OPr- 2-Py], [0997: 6-Cl-5-OPr-2-Py], [0998: 3-Me-5-OPr-2-Py], [0999: 4-Me-5-OPr-2- Py], [1000: 6-Me-5-OPr-2-Py],
[1001:3−CF3−5−OPr−2−Py]、[1002:4−CF3−5−OPr−2−Py]、[1003:6−CF3−5−OPr−2−Py]、[1004:3−CN−5−OPr−2−Py]、[1005:4−CN−5−OPr−2−Py]、[1006:6−CN−5−OPr−2−Py]、[1007:3−OMe−5−OPr−2−Py]、[1008:4−OMe−5−OPr−2−Py]、[1009:6−OMe−5−OPr−2−Py]、[1010:6−OPr−2−Py]、[1011:3−Cl−6−OPr−2−Py]、[1012:4−Cl−6−OPr−2−Py]、[1013:5−Cl−6−OPr−2−Py]、[1014:3−Me−6−OPr−2−Py]、[1015:4−Me−6−OPr−2−Py]、[1016:5−Me−6−OPr−2−Py]、[1017:3−CF3−6−OPr−2−Py]、[1018:4−CF3−6−OPr−2−Py]、[1019:5−CF3−6−OPr−2−Py]、[1020:3−CN−6−OPr−2−Py]、[1021:4−CN−6−OPr−2−Py]、[1022:5−CN−6−OPr−2−Py]、[1023:3−OMe−6−OPr−2−Py]、[1024:4−OMe−6−OPr−2−Py]、[1025:5−OMe−6−OPr−2−Py]、[1026:3−SMe−2−Py]、[1027:4−Cl−3−SMe−2−Py]、[1028:5−Cl−3−SMe−2−Py]、[1029:6−Cl−3−SMe−2−Py]、[1030:4−Me−3−SMe−2−Py]、[1031:5−Me−3−SMe−2−Py]、[1032:6−Me−3−SMe−2−Py]、[1033:4−CF3−3−SMe−2−Py]、[1034:5−CF3−3−SMe−2−Py]、[1035:6−CF3−3−SMe−2−Py]、[1036:4−CN−3−SMe−2−Py]、[1037:5−CN−3−SMe−2−Py]、[1038:6−CN−3−SMe−2−Py]、[1039:4−OMe−3−SMe−2−Py]、[1040:5−OMe−3−SMe−2−Py]、[1041:6−OMe−3−SMe−2−Py]、[1042:4−SMe−2−Py]、[1043:3−Cl−4−SMe−2−Py]、[1044:5−Cl−4−SMe−2−Py]、[1045:6−Cl−4−SMe−2−Py]、[1046:3−Me−4−SMe−2−Py]、[1047:5−Me−4−SMe−2−Py]、[1048:6−Me−4−SMe−2−Py]、[1049:3−CF3−4−SMe−2−Py]、[1050:5−CF3−4−SMe−2−Py]、[1051:6−CF3−4−SMe−2−Py]、[1052:3−CN−4−SMe−2−Py]、[1053:5−CN−4−SMe−2−Py]、[1054:6−CN−4−SMe−2−Py]、[1055:3−OMe−4−SMe−2−Py]、[1056:5−OMe−4−SMe−2−Py]、[1057:6−OMe−4−SMe−2−Py]、[1058:5−SMe−2−Py]、[1059:3−Cl−5−SMe−2−Py]、[1060:4−Cl−5−SMe−2−Py]、[1061:6−Cl−5−SMe−2−Py]、[1062:3−Me−5−SMe−2−Py]、[1063:4−Me−5−SMe−2−Py]、[1064:6−Me−5−SMe−2−Py]、[1065:3−CF3−5−SMe−2−Py]、[1066:4−CF3−5−SMe−2−Py]、[1067:6−CF3−5−SMe−2−Py]、[1068:3−CN−5−SMe−2−Py]、[1069:4−CN−5−SMe−2−Py]、[1070:6−CN−5−SMe−2−Py]、[1071:3−OMe−5−SMe−2−Py]、[1072:4−OMe−5−SMe−2−Py]、[1073:6−OMe−5−SMe−2−Py]、[1074:6−SMe−2−Py]、[1075:3−Cl−6−SMe−2−Py]、[1076:4−Cl−6−SMe−2−Py]、[1077:5−Cl−6−SMe−2−Py]、[1078:3−Me−6−SMe−2−Py]、[1079:4−Me−6−SMe−2−Py]、[1080:5−Me−6−SMe−2−Py]、[1081:3−CF3−6−SMe−2−Py]、[1082:4−CF3−6−SMe−2−Py]、[1083:5−CF3−6−SMe−2−Py]、[1084:3−CN−6−SMe−2−Py]、[1085:4−CN−6−SMe−2−Py]、[1086:5−CN−6−SMe−2−Py]、[1087:3−OMe−6−SMe−2−Py]、[1088:4−OMe−6−SMe−2−Py]、[1089:5−OMe−6−SMe−2−Py]、[1090:3−SCF3−2−Py]、[1091:4−Cl−3−SCF3−2−Py]、[1092:5−Cl−3−SCF3−2−Py]、[1093:6−Cl−3−SCF3−2−Py]、[1094:4−Me−3−SCF3−2−Py]、[1095:5−Me−3−SCF3−2−Py]、[1096:6−Me−3−SCF3−2−Py]、[1097:4−CF3−3−SCF3−2−Py]、[1098:5−CF3−3−SCF3−2−Py]、[1099:6−CF3−3−SCF3−2−Py]、[1100:4−CN−3−SCF3−2−Py]、 [1001: 3-CF3-5-OPr-2-Py], [1002: 4-CF3-5-OPr-2-Py], [1003: 6-CF3-5-OPr-2-Py], [1004 : 3-CN-5-OPr-2-Py], [1005: 4-CN-5-OPr-2-Py], [1006: 6-CN-5-OPr-2-Py], [1007: 3 -OMe-5-OPr-2-Py], [1008: 4-OMe-5-OPr-2-Py], [1009: 6-OMe-5-OPr-2-Py], [1010: 6-OPr -2-Py], [1011: 3-Cl-6-OPr-2-Py], [1012: 4-Cl-6-OPr-2-Py], [1013: 5-Cl-6-OPr-2 -Py], [1014: 3-Me-6-OPr-2-Py], [1015: 4-Me 6-OPr-2-Py], [1016: 5-Me-6-OPr-2-Py], [1017: 3-CF3-6-OPr-2-Py], [1018: 4-CF3-6 OPr-2-Py], [1019: 5-CF3-6-OPr-2-Py], [1020: 3-CN-6-OPr-2-Py], [1021: 4-CN-6-OPr- 2-Py], [1022: 5-CN-6-OPr-2-Py], [1023: 3-OMe-6-OPr-2-Py], [1024: 4-OMe-6-OPr-2- Py], [1025: 5-OMe-6-OPr-2-Py], [1026: 3-SMe-2-Py], [1027: 4-Cl-3-SMe-2-Py], [1028: 5-Cl-3-SMe-2-Py], [1029: 6-Cl-3-SMe-2-P ], [1030: 4-Me-3-SMe-2-Py], [1031: 5-Me-3-SMe-2-Py], [1032: 6-Me-3-SMe-2-Py], [1033: 4-CF3-3-3-SMe-2-Py], [1034: 5-CF3-3-SMe-2-Py], [1035: 6-CF3-3-SMe-2-Py], [1036 : 4-CN-3-SMe-2-Py], [1037: 5-CN-3-SMe-2-Py], [1038: 6-CN-3-SMe-2-Py], [1039: 4 -OMe-3-SMe-2-Py], [1040: 5-OMe-3-SMe-2-Py], [1041: 6-OMe-3-SMe-2-Py], [1042: 4-SMe -2-Py], [1043: 3-Cl-4-SMe-2-Py], [1044: 5- Cl-4-SMe-2-Py], [1045: 6-Cl-4-SMe-2-Py], [1046: 3-Me-4-SMe-2-Py], [1047: 5-Me- 4-SMe-2-Py], [1048: 6-Me-4-SMe-2-Py], [1049: 3-CF3-4-SMe-2-Py], [1050: 5-CF3-4- SMe-2-Py], [1051: 6-CF3-4-SMe-2-Py], [1052: 3-CN-4-SMe-2-Py], [1053: 5-CN-4-SMe- 2-Py], [1054: 6-CN-4-SMe-2-Py], [1055: 3-OMe-4-SMe-2-Py], [1056: 5-OMe-4-SMe-2- Py], [1057: 6-OMe-4-SMe-2-Py], [1058: 5-SMe-2 Py], [1059: 3-Cl-5-SMe-2-Py], [1060: 4-Cl-5-SMe-2-Py], [1061: 6-Cl-5-SMe-2-Py] [1062: 3-Me-5-SMe-2-Py], [1063: 4-Me-5-SMe-2-Py], [1064: 6-Me-5-SMe-2-Py], [ 1065: 3-CF3-5-SMe-2-Py], [1066: 4-CF3-5-SMe-2-Py], [1067: 6-CF3-5-SMe-2-Py], [1068: 3-CN-5-SMe-2-Py], [1069: 4-CN-5-SMe-2-Py], [1070: 6-CN-5-SMe-2-Py], [1071: 3- OMe-5-SMe-2-Py], [1072: 4-OMe-5-SMe-2-Py], [ 073: 6-OMe-5-SMe-2-Py], [1074: 6-SMe-2-Py], [1075: 3-Cl-6-SMe-2-Py], [1076: 4-Cl- 6-SMe-2-Py], [1077: 5-Cl-6-SMe-2-Py], [1078: 3-Me-6-SMe-2-Py], [1079: 4-Me-6-6 SMe-2-Py], [1080: 5-Me-6-SMe-2-Py], [1081: 3-CF3-6-SMe-2-Py], [1082: 4-CF3-6-SMe- 2-Py], [1083: 5-CF3-6-SMe-2-Py], [1084: 3-CN-6-SMe-2-Py], [1085: 4-CN-6-SMe-2- Py], [1086: 5-CN-6-SMe-2-Py], [1087: 3-OMe-6-6 SMe-2-Py], [1088: 4-OMe-6-SMe-2-Py], [1089: 5-OMe-6-SMe-2-Py], [1090: 3-SCF3-2-Py] [1091: 4-Cl-3-SCF3-2-Py], [1092: 5-Cl-3-SCF3-2-Py], [1093: 6-Cl-3-SCF3-2-Py], [ 1094: 4-Me-3-SCF3-2-Py], [1095: 5-Me-3-SCF3-2-Py], [1096: 6-Me-3-SCF3-2-Py], [1097: 4-CF3-3-SCF3-2-Py], [1098: 5-CF3-3-SCF3-2-Py], [1099: 6-CF3-3-SCF3-2-Py], [1100: 4- CN-3-SCF3-2-Py],
[1101:5−CN−3−SCF3−2−Py]、[1102:6−CN−3−SCF3−2−Py]、[1103:4−OMe−3−SCF3−2−Py]、[1104:5−OMe−3−SCF3−2−Py]、[1105:6−OMe−3−SCF3−2−Py]、[1106:4−SCF3−2−Py]、[1107:3−Cl−4−SCF3−2−Py]、[1108:5−Cl−4−SCF3−2−Py]、[1109:6−Cl−4−SCF3−2−Py]、[1110:3−Me−4−SCF3−2−Py]、[1111:5−Me−4−SCF3−2−Py]、[1112:6−Me−4−SCF3−2−Py]、[1113:3−CF3−4−SCF3−2−Py]、[1114:5−CF3−4−SCF3−2−Py]、[1115:6−CF3−4−SCF3−2−Py]、[1116:3−CN−4−SCF3−2−Py]、[1117:5−CN−4−SCF3−2−Py]、[1118:6−CN−4−SCF3−2−Py]、[1119:3−OMe−4−SCF3−2−Py]、[1120:5−OMe−4−SCF3−2−Py]、[1121:6−OMe−4−SCF3−2−Py]、[1122:5−SCF3−2−Py]、[1123:3−Cl−5−SCF3−2−Py]、[1124:4−Cl−5−SCF3−2−Py]、[1125:6−Cl−5−SCF3−2−Py]、[1126:3−Me−5−SCF3−2−Py]、[1127:4−Me−5−SCF3−2−Py]、[1128:6−Me−5−SCF3−2−Py]、[1129:3−CF3−5−SCF3−2−Py]、[1130:4−CF3−5−SCF3−2−Py]、[1131:6−CF3−5−SCF3−2−Py]、[1132:3−CN−5−SCF3−2−Py]、[1133:4−CN−5−SCF3−2−Py]、[1134:6−CN−5−SCF3−2−Py]、[1135:3−OMe−5−SCF3−2−Py]、[1136:4−OMe−5−SCF3−2−Py]、[1137:6−OMe−5−SCF3−2−Py]、[1138:6−SCF3−2−Py]、[1139:3−Cl−6−SCF3−2−Py]、[1140:4−Cl−6−SCF3−2−Py]、[1141:6−Cl−6−SCF3−2−Py]、[1142:3−Me−6−SCF3−2−Py]、[1143:4−Me−6−SCF3−2−Py]、[1144:6−Me−6−SCF3−2−Py]、[1145:3−CF3−6−SCF3−2−Py]、[1146:4−CF3−6−SCF3−2−Py]、[1147:6−CF3−6−SCF3−2−Py]、[1148:3−CN−6−SCF3−2−Py]、[1149:4−CN−6−SCF3−2−Py]、[1150:6−CN−6−SCF3−2−Py]、[1151:3−OMe−6−SCF3−2−Py]、[1152:4−OMe−6−SCF3−2−Py]、[1153:6−OMe−6−SCF3−2−Py]、[1154:3−S(O)Me−2−Py]、[1155:4−Cl−3−S(O)Me−2−Py]、[1156:5−Cl−3−S(O)Me−2−Py]、[1157:6−Cl−3−S(O)Me−2−Py]、[1158:4−Me−3−S(O)Me−2−Py]、[1159:5−Me−3−S(O)Me−2−Py]、[1160:6−Me−3−S(O)Me−2−Py]、[1161:4−CF3−3−S(O)Me−2−Py]、[1162:5−CF3−3−S(O)Me−2−Py]、[1163:6−CF3−3−S(O)Me−2−Py]、[1164:4−CN−3−S(O)Me−2−Py]、[1165:5−CN−3−S(O)Me−2−Py]、[1166:6−CN−3−S(O)Me−2−Py]、[1167:4−OMe−3−S(O)Me−2−Py]、[1168:5−OMe−3−S(O)Me−2−Py]、[1169:6−OMe−3−S(O)Me−2−Py]、[1170:4−S(O)Me−2−Py]、[1171:3−Cl−4−S(O)Me−2−Py]、[1172:5−Cl−4−S(O)Me−2−Py]、[1173:6−Cl−4−S(O)Me−2−Py]、[1174:3−Me−4−S(O)Me−2−Py]、[1175:5−Me−4−S(O)Me−2−Py]、[1176:6−Me−4−S(O)Me−2−Py]、[1177:3−CF3−4−S(O)Me−2−Py]、[1178:5−CF3−4−S(O)Me−2−Py]、[1179:6−CF3−4−S(O)Me−2−Py]、[1180:3−CN−4−S(O)Me−2−Py]、[1181:5−CN−4−S(O)Me−2−Py]、[1182:6−CN−4−S(O)Me−2−Py]、[1183:3−OMe−4−S(O)Me−2−Py]、[1184:5−OMe−4−S(O)Me−2−Py]、[1185:6−OMe−4−S(O)Me−2−Py]、[1186:5−S(O)Me−2−Py]、[1187:3−Cl−5−S(O)Me−2−Py]、[1188:4−Cl−5−S(O)Me−2−Py]、[1189:6−Cl−5−S(O)Me−2−Py]、[1190:3−Me−5−S(O)Me−2−Py]、[1191:4−Me−5−S(O)Me−2−Py]、[1192:6−Me−5−S(O)Me−2−Py]、[1193:3−CF3−5−S(O)Me−2−Py]、[1194:4−CF3−5−S(O)Me−2−Py]、[1195:6−CF3−5−S(O)Me−2−Py]、[1196:3−CN−5−S(O)Me−2−Py]、[1197:4−CN−5−S(O)Me−2−Py]、[1198:6−CN−5−S(O)Me−2−Py]、[1199:3−OMe−5−S(O)Me−2−Py]、[1200:4−OMe−5−S(O)Me−2−Py]、 [1101: 5-CN-3-SCF3-2-Py], [1102: 6-CN-3-SCF3-2-Py], [1103: 4-OMe-3-SCF3-2-Py], [1104 : 5-OMe-3-SCF3-2-Py], [1105: 6-OMe-3-SCF3-2-Py], [1106: 4-SCF3-2-Py], [1107: 3-Cl-4 -SCF3-2-Py], [1108: 5-Cl-4-SCF3-2-Py], [1109: 6-Cl-4-SCF3-2-Py], [1110: 3-Me-4-SCF3 -2-Py], [1111: 5-Me-4-SCF3-2-Py], [1112: 6-Me-4-SCF3-2-Py], [1113: 3-CF3-4-SCF3-2 -Py], [1114: 5-CF3-4-SCF3-2-P ], [1115: 6-CF3-4-SCF3-2-Py], [1116: 3-CN-4-SCF3-2-Py], [1117: 5-CN-4-SCF3-2-Py], [1118: 6-CN-4-SCF3-2-Py], [1119: 3-OMe-4-SCF3-2-Py], [1120: 5-OMe-4-SCF3-2-Py], [1121 : 6-OMe-4-SCF3-2-Py], [1122: 5-SCF3-2-Py], [1123: 3-Cl-5-SCF3-2-Py], [1124: 4-Cl-5 -SCF3-2-Py], [1125: 6-Cl-5-SCF3-2-Py], [1126: 3-Me-5-SCF3-2-Py], [1127: 4-Me-5-SCF3 -2-Py], [1128: 6-Me-5-SCF3-2 Py], [1129: 3-CF3-5-SCF3-2-Py], [1130: 4-CF3-5-SCF3-2-Py], [1131: 6-CF3-5-SCF3-2-Py] [1132: 3-CN-5-SCF3-2-Py], [1133: 4-CN-5-SCF3-2-Py], [1134: 6-CN-5-SCF3-2-Py], [ 1135: 3-OMe-5-SCF3-2-Py], [1136: 4-OMe-5-SCF3-2-Py], [1137: 6-OMe-5-SCF3-2-Py], [1138: 6-SCF3-2-Py], [1139: 3-Cl-6-SCF3-2-Py], [1140: 4-Cl-6-SCF3-2-Py], [1141: 6-Cl-6 SCF3-2-Py], [1142: 3-Me-6-SCF 3-2-Py], [1143: 4-Me-6-SCF3-2-Py], [1144: 6-Me-6-SCF3-2-Py], [1145: 3-CF3-6-SCF3- 2-Py], [1146: 4-CF3-6-SCF3-2-Py], [1147: 6-CF3-6-SCF3-2-Py], [1148: 3-CN-6-SCF3-2- Py], [1149: 4-CN-6-SCF3-2-Py], [1150: 6-CN-6-SCF3-2-Py], [1151: 3-OMe-6-SCF3-2-Py] [1152: 4-OMe-6-SCF3-2-Py], [1153: 6-OMe-6-SCF3-2-Py], [1154: 3-S (O) Me-2-Py], [ 1155: 4-Cl-3-S (O) Me-2-Py], [1156: 5- l-3-S (O) Me-2-Py], [1157: 6-Cl-3-S (O) Me-2-Py], [1158: 4-Me-3-S (O) Me- 2-Py], [1159: 5-Me-3-S (O) Me-2-Py], [1160: 6-Me-3-S (O) Me-2-Py], [1161: 4- CF3-3-S (O) Me-2-Py], [1162: 5-CF3-3-S (O) Me-2-Py], [1163: 6-CF3-3-S (O) Me- 2-Py], [1164: 4-CN-3-S (O) Me-2-Py], [1165: 5-CN-3-S (O) Me-2-Py], [1166: 6- CN-3-S (O) Me-2-Py], [1167: 4-OMe-3-S (O) Me-2-Py], [1168: 5-OMe-3-S (O) Me- 2-Py [1169: 6-OMe-3-S (O) Me-2-Py], [1170: 4-S (O) Me-2-Py], [1171: 3-Cl-4-S (O) Me-2-Py], [1172: 5-Cl-4-S (O) Me-2-Py], [1173: 6-Cl-4-S (O) Me-2-Py], [1174: 3-Me-4-S (O) Me-2-Py], [1175: 5-Me-4-S (O) Me-2-Py], [1176: 6-Me-4-S (O) Me-2-Py], [1177: 3-CF3-4-S (O) Me-2-Py], [1178: 5-CF3-4-S (O) Me-2-Py], [1179: 6-CF3-4-S (O) Me-2-Py], [1180: 3-CN-4-S (O) Me-2-Py], [1181: 5-CN-4-S (O) Me-2 -Py], [1182: 6-CN-4-S (O) Me-2-Py], [1183: 3-OMe-4-S (O) Me-2-Py], [1184: 5-OMe. -4-S (O) Me-2-Py], [1185: 6-OMe-4-S (O) Me-2-Py], [1186: 5-S (O) Me-2-Py], [1187: 3-Cl-5-S (O) Me-2-Py], [1188: 4-Cl-5-S (O) Me-2-Py], [1189: 6-Cl-5-S (O) Me-2-Py], [1190: 3-Me-5-S (O) Me-2-Py], [1191: 4-Me-5-S (O) Me-2-Py], [1192: 6-Me-5-S (O) Me-2-Py], [1193: 3-CF3-5-S (O) Me-2-Py], [1194: 4-CF3-5-S (O Me-2-Py], [1195: 6-CF3-5-S (O) Me-2-Py], [1196: 3-CN-5-S (O) Me-2-Py], [1197: 4-CN-5-S (O) Me-2-Py], [1198: 6-CN-5-S (O) Me-2-Py], [1199: 3-OMe-5-S (O) Me-2-Py], [1200: 4-OMe-5-S (O) Me-2-Py],
[1201:6−OMe−5−S(O)Me−2−Py]、[1202:6−S(O)Me−2−Py]、[1203:3−Cl−6−S(O)Me−2−Py]、[1204:4−Cl−6−S(O)Me−2−Py]、[1205:5−Cl−6−S(O)Me−2−Py]、[1206:3−Me−6−S(O)Me−2−Py]、[1207:4−Me−6−S(O)Me−2−Py]、[1208:5−Me−6−S(O)Me−2−Py]、[1209:3−CF3−6−S(O)Me−2−Py]、[1210:4−CF3−6−S(O)Me−2−Py]、[1211:5−CF3−6−S(O)Me−2−Py]、[1212:3−CN−6−S(O)Me−2−Py]、[1213:4−CN−6−S(O)Me−2−Py]、[1214:5−CN−6−S(O)Me−2−Py]、[1215:3−OMe−6−S(O)Me−2−Py]、[1216:4−OMe−6−S(O)Me−2−Py]、[1217:5−OMe−6−S(O)Me−2−Py]、[1218:3−S(O)CF3−2−Py]、[1219:4−Cl−3−S(O)CF3−2−Py]、[1220:5−Cl−3−S(O)CF3−2−Py]、[1221:6−Cl−3−S(O)CF3−2−Py]、[1222:4−Me−3−S(O)CF3−2−Py]、[1223:5−Me−3−S(O)CF3−2−Py]、[1224:6−Me−3−S(O)CF3−2−Py]、[1225:4−CF3−3−S(O)CF3−2−Py]、[1226:5−CF3−3−S(O)CF3−2−Py]、[1227:6−CF3−3−S(O)CF3−2−Py]、[1228:4−CN−3−S(O)CF3−2−Py]、[1229:5−CN−3−S(O)CF3−2−Py]、[1230:6−CN−3−S(O)CF3−2−Py]、[1231:4−OMe−3−S(O)CF3−2−Py]、[1232:5−OMe−3−S(O)CF3−2−Py]、[1233:6−OMe−3−S(O)CF3−2−Py]、[1234:4−S(O)CF3−2−Py]、[1235:3−Cl−4−S(O)CF3−2−Py]、[1236:5−Cl−4−S(O)CF3−2−Py]、[1237:6−Cl−4−S(O)CF3−2−Py]、[1238:3−Me−4−S(O)CF3−2−Py]、[1239:5−Me−4−S(O)CF3−2−Py]、[1240:6−Me−4−S(O)CF3−2−Py]、[1241:3−CF3−4−S(O)CF3−2−Py]、[1242:5−CF3−4−S(O)CF3−2−Py]、[1243:6−CF3−4−S(O)CF3−2−Py]、[1244:3−CN−4−S(O)CF3−2−Py]、[1245:5−CN−4−S(O)CF3−2−Py]、[1246:6−CN−4−S(O)CF3−2−Py]、[1247:3−OMe−4−S(O)CF3−2−Py]、[1248:5−OMe−4−S(O)CF3−2−Py]、[1249:6−OMe−4−S(O)CF3−2−Py]、[1250:5−S(O)CF3−2−Py]、[1251:3−Cl−5−S(O)CF3−2−Py]、[1252:4−Cl−5−S(O)CF3−2−Py]、[1253:6−Cl−5−S(O)CF3−2−Py]、[1254:3−Me−5−S(O)CF3−2−Py]、[1255:4−Me−5−S(O)CF3−2−Py]、[1256:6−Me−5−S(O)CF3−2−Py]、[1257:3−CF3−5−S(O)CF3−2−Py]、[1258:4−CF3−5−S(O)CF3−2−Py]、[1259:6−CF3−5−S(O)CF3−2−Py]、[1260:3−CN−5−S(O)CF3−2−Py]、[1261:4−CN−5−S(O)CF3−2−Py]、[1262:6−CN−5−S(O)CF3−2−Py]、[1263:3−OMe−5−S(O)CF3−2−Py]、[1264:4−OMe−5−S(O)CF3−2−Py]、[1265:6−OMe−5−S(O)CF3−2−Py]、[1266:6−S(O)CF3−2−Py]、[1267:3−Cl−6−S(O)CF3−2−Py]、[1268:4−Cl−6−S(O)CF3−2−Py]、[1269:5−Cl−6−S(O)CF3−2−Py]、[1270:3−Me−6−S(O)CF3−2−Py]、[1271:4−Me−6−S(O)CF3−2−Py]、[1272:5−Me−6−S(O)CF3−2−Py]、[1273:3−CF3−6−S(O)CF3−2−Py]、[1274:4−CF3−6−S(O)CF3−2−Py]、[1275:5−CF3−6−S(O)CF3−2−Py]、[1276:3−CN−6−S(O)CF3−2−Py]、[1277:4−CN−6−S(O)CF3−2−Py]、[1278:5−CN−6−S(O)CF3−2−Py]、[1279:3−OMe−6−S(O)CF3−2−Py]、[1280:4−OMe−6−S(O)CF3−2−Py]、[1281:5−OMe−6−S(O)CF3−2−Py]、[1282:3−S(O)2Me−2−Py]、[1283:4−Cl−3−S(O)2Me−2−Py]、[1284:5−Cl−3−S(O)2Me−2−Py]、[1285:6−Cl−3−S(O)2Me−2−Py]、[1286:4−Me−3−S(O)2Me−2−Py]、[1287:5−Me−3−S(O)2Me−2−Py]、[1288:6−Me−3−S(O)2Me−2−Py]、[1289:4−CF3−3−S(O)2Me−2−Py]、[1290:5−CF3−3−S(O)2Me−2−Py]、[1291:6−CF3−3−S(O)2Me−2−Py]、[1292:4−CN−3−S(O)2Me−2−Py]、[1293:5−CN−3−S(O)2Me−2−Py]、[1294:6−CN−3−S(O)2Me−2−Py]、[1295:4−OMe−3−S(O)2Me−2−Py]、[1296:5−OMe−3−S(O)2Me−2−Py]、[1297:6−OMe−3−S(O)2Me−2−Py]、[1298:4−S(O)2Me−2−Py]、[1299:3−Cl−4−S(O)2Me−2−Py]、[1300:5−Cl−4−S(O)2Me−2−Py]、 [1201: 6-OMe-5-S (O) Me-2-Py], [1202: 6-S (O) Me-2-Py], [1203: 3-Cl-6-S (O) Me -2-Py], [1204: 4-Cl-6-S (O) Me-2-Py], [1205: 5-Cl-6-S (O) Me-2-Py], [1206: 3 -Me-6-S (O) Me-2-Py], [1207: 4-Me-6-S (O) Me-2-Py], [1208: 5-Me-6-S (O) Me -2-Py], [1209: 3-CF3-6-S (O) Me-2-Py], [1210: 4-CF3-6-S (O) Me-2-Py], [1211: 5 -CF3-6-S (O) Me-2-Py], [1212: 3-CN-6-S (O) Me-2-Py], [1213: 4-CN-6-S (O) Me -2- y], [1214: 5-CN-6-S (O) Me-2-Py], [1215: 3-OMe-6-S (O) Me-2-Py], [1216: 4-OMe- 6-S (O) Me-2-Py], [1217: 5-OMe-6-S (O) Me-2-Py], [1218: 3-S (O) CF3-2-Py], [ 1219: 4-Cl-3-S (O) CF3-2-Py], [1220: 5-Cl-3-S (O) CF3-2-Py], [1221: 6-Cl-3-S ( O) CF3-2-Py], [1222: 4-Me-3-S (O) CF3-2-Py], [1223: 5-Me-3-S (O) CF3-2-Py], [ 1224: 6-Me-3-S (O) CF3-2-Py], [1225: 4-CF3-3-S (O) CF3-2-Py], [1226: 5-CF -3-S (O) CF3-2-Py], [1227: 6-CF3-3-S (O) CF3-2-Py], [1228: 4-CN-3-S (O) CF3-2 -Py], [1229: 5-CN-3-S (O) CF3-2-Py], [1230: 6-CN-3-S (O) CF3-2-Py], [1231: 4-OMe -3-S (O) CF3-2-Py], [1232: 5-OMe-3-S (O) CF3-2-Py], [1233: 6-OMe-3-S (O) CF3-2 -Py], [1234: 4-S (O) CF3-2-Py], [1235: 3-Cl-4-S (O) CF3-2-Py], [1236: 5-Cl-4-S (O) CF3-2-Py], [1237: 6-Cl-4-S (O) CF3-2-Py], [1238: 3-Me-4-S (O) CF3 -2-Py], [1239: 5-Me-4-S (O) CF3-2-Py], [1240: 6-Me-4-S (O) CF3-2-Py], [1241: 3 -CF3-4-S (O) CF3-2-Py], [1242: 5-CF3-4-S (O) CF3-2-Py], [1243: 6-CF3-4-S (O) CF3 -2-Py], [1244: 3-CN-4-S (O) CF3-2-Py], [1245: 5-CN-4-S (O) CF3-2-Py], [1246: 6 -CN-4-S (O) CF3-2-Py], [1247: 3-OMe-4-S (O) CF3-2-Py], [1248: 5-OMe-4-S (O) CF3 -2-Py], [1249: 6-OMe-4-S (O) CF3-2-Py], [1250: 5-S (O) CF3-2-Py], [ 251: 3-Cl-5-S (O) CF3-2-Py], [1252: 4-Cl-5-S (O) CF3-2-Py], [1253: 6-Cl-5-S ( O) CF3-2-Py], [1254: 3-Me-5-S (O) CF3-2-Py], [1255: 4-Me-5-S (O) CF3-2-Py], [ 1256: 6-Me-5-S (O) CF3-2-Py], [1257: 3-CF3-5-S (O) CF3-2-Py], [1258: 4-CF3-5-S ( O) CF3-2-Py], [1259: 6-CF3-5-S (O) CF3-2-Py], [1260: 3-CN-5-S (O) CF3-2-Py], [ 1261: 4-CN-5-S (O) CF3-2-Py], [1262: 6-CN-5-S (O) CF3-2-Py], [1263: 3 OMe-5-S (O) CF3-2-Py], [1264: 4-OMe-5-S (O) CF3-2-Py], [1265: 6-OMe-5-S (O) CF3- 2-Py], [1266: 6-S (O) CF3-2-Py], [1267: 3-Cl-6-S (O) CF3-2-Py], [1268: 4-Cl-6- S (O) CF3-2-Py], [1269: 5-Cl-6-S (O) CF3-2-Py], [1270: 3-Me-6-S (O) CF3-2-Py] [1271: 4-Me-6-S (O) CF3-2-Py], [1272: 5-Me-6-S (O) CF3-2-Py], [1273: 3-CF3-6 S (O) CF3-2-Py], [1274: 4-CF3-6-S (O) CF3-2-Py], [1275: 5-CF3-6-S (O ) CF3-2-Py], [1276: 3-CN-6-S (O) CF3-2-Py], [1277: 4-CN-6-S (O) CF3-2-Py], [1278 : 5-CN-6-S (O) CF3-2-Py], [1279: 3-OMe-6-S (O) CF3-2-Py], [1280: 4-OMe-6-S (O ) CF3-2-Py], [1281: 5-OMe-6-S (O) CF3-2-Py], [1282: 3-S (O) 2Me-2-Py], [1283: 4-Cl -3-S (O) 2Me-2-Py], [1284: 5-Cl-3-S (O) 2Me-2-Py], [1285: 6-Cl-3-S (O) 2Me-2 -Py], [1286: 4-Me-3-S (O) 2Me-2-Py], [1287: 5-Me-3-S (O) 2Me-2-Py], 1288: 6-Me-3-S (O) 2Me-2-Py], [1289: 4-CF3-3-S (O) 2Me-2-Py], [1290: 5-CF3-3-S ( O) 2Me-2-Py], [1291: 6-CF3-3-3-S (O) 2Me-2-Py], [1292: 4-CN-3-S (O) 2Me-2-Py], [ 1293: 5-CN-3-S (O) 2Me-2-Py], [1294: 6-CN-3-S (O) 2Me-2-Py], [1295: 4-OMe-3-S ( O) 2Me-2-Py], [1296: 5-OMe-3-S (O) 2Me-2-Py], [1297: 6-OMe-3-S (O) 2Me-2-Py], [ 1298: 4-S (O) 2Me-2-Py], [1299: 3-Cl-4-S (O) 2Me-2-Py], [1300: 5- l-4-S (O) 2Me-2-Py],
[1301:6−Cl−4−S(O)2Me−2−Py]、[1302:3−Me−4−S(O)2Me−2−Py]、[1303:5−Me−4−S(O)2Me−2−Py]、[1304:6−Me−4−S(O)2Me−2−Py]、[1305:3−CF3−4−S(O)2Me−2−Py]、[1306:5−CF3−4−S(O)2Me−2−Py]、[1307:6−CF3−4−S(O)2Me−2−Py]、[1308:3−CN−4−S(O)2Me−2−Py]、[1309:5−CN−4−S(O)2Me−2−Py]、[1310:6−CN−4−S(O)2Me−2−Py]、[1311:3−OMe−4−S(O)2Me−2−Py]、[1312:5−OMe−4−S(O)2Me−2−Py]、[1313:6−OMe−4−S(O)2Me−2−Py]、[1314:5−S(O)2Me−2−Py]、[1315:3−Cl−5−S(O)2Me−2−Py]、[1316:4−Cl−5−S(O)2Me−2−Py]、[1317:6−Cl−5−S(O)2Me−2−Py]、[1318:3−Me−5−S(O)2Me−2−Py]、[1319:4−Me−5−S(O)2Me−2−Py]、[1320:6−Me−5−S(O)2Me−2−Py]、[1321:3−CF3−5−S(O)2Me−2−Py]、[1322:4−CF3−5−S(O)2Me−2−Py]、[1323:6−CF3−5−S(O)2Me−2−Py]、[1324:3−CN−5−S(O)2Me−2−Py]、[1325:4−CN−5−S(O)2Me−2−Py]、[1326:6−CN−5−S(O)2Me−2−Py]、[1327:3−OMe−5−S(O)2Me−2−Py]、[1328:4−OMe−5−S(O)2Me−2−Py]、[1329:6−OMe−5−S(O)2Me−2−Py]、[1330:6−S(O)2Me−2−Py]、[1331:3−Cl−6−S(O)2Me−2−Py]、[1332:4−Cl−6−S(O)2Me−2−Py]、[1333:5−Cl−6−S(O)2Me−2−Py]、[1334:3−Me−6−S(O)2Me−2−Py]、[1335:4−Me−6−S(O)2Me−2−Py]、[1336:5−Me−6−S(O)2Me−2−Py]、[1337:3−CF3−6−S(O)2Me−2−Py]、[1338:4−CF3−6−S(O)2Me−2−Py]、[1339:5−CF3−6−S(O)2Me−2−Py]、[1340:3−CN−6−S(O)2Me−2−Py]、[1341:4−CN−6−S(O)2Me−2−Py]、[1342:5−CN−6−S(O)2Me−2−Py]、[1343:3−OMe−6−S(O)2Me−2−Py]、[1344:4−OMe−6−S(O)2Me−2−Py]、[1345:5−OMe−6−S(O)2Me−2−Py]、[1346:3−S(O)2CF3−2−Py]、[1347:4−Cl−3−S(O)2CF3−2−Py]、[1348:5−Cl−3−S(O)2CF3−2−Py]、[1349:6−Cl−3−S(O)2CF3−2−Py]、[1350:4−Me−3−S(O)2CF3−2−Py]、[1351:5−Me−3−S(O)2CF3−2−Py]、[1352:6−Me−3−S(O)2CF3−2−Py]、[1353:4−CF3−3−S(O)2CF3−2−Py]、[1354:5−CF3−3−S(O)2CF3−2−Py]、[1355:6−CF3−3−S(O)2CF3−2−Py]、[1356:4−CN−3−S(O)2CF3−2−Py]、[1357:5−CN−3−S(O)2CF3−2−Py]、[1358:6−CN−3−S(O)2CF3−2−Py]、[1359:4−OMe−3−S(O)2CF3−2−Py]、[1360:5−OMe−3−S(O)2CF3−2−Py]、[1361:6−OMe−3−S(O)2CF3−2−Py]、[1362:4−S(O)2CF3−2−Py]、[1363:3−Cl−4−S(O)2CF3−2−Py]、[1364:5−Cl−4−S(O)2CF3−2−Py]、[1365:6−Cl−4−S(O)2CF3−2−Py]、[1366:3−Me−4−S(O)2CF3−2−Py]、[1367:5−Me−4−S(O)2CF3−2−Py]、[1368:6−Me−4−S(O)2CF3−2−Py]、[1369:3−CF3−4−S(O)2CF3−2−Py]、[1370:5−CF3−4−S(O)2CF3−2−Py]、[1371:6−CF3−4−S(O)2CF3−2−Py]、[1372:3−CN−4−S(O)2CF3−2−Py]、[1373:5−CN−4−S(O)2CF3−2−Py]、[1374:6−CN−4−S(O)2CF3−2−Py]、[1375:3−OMe−4−S(O)2CF3−2−Py]、[1376:5−OMe−4−S(O)2CF3−2−Py]、[1377:6−OMe−4−S(O)2CF3−2−Py]、[1378:5−S(O)2CF3−2−Py]、[1379:3−Cl−5−S(O)2CF3−2−Py]、[1380:4−Cl−5−S(O)2CF3−2−Py]、[1381:6−Cl−5−S(O)2CF3−2−Py]、[1382:3−Me−5−S(O)2CF3−2−Py]、[1383:4−Me−5−S(O)2CF3−2−Py]、[1384:6−Me−5−S(O)2CF3−2−Py]、[1385:3−CF3−5−S(O)2CF3−2−Py]、[1386:4−CF3−5−S(O)2CF3−2−Py]、[1387:6−CF3−5−S(O)2CF3−2−Py]、[1388:3−CN−5−S(O)2CF3−2−Py]、[1389:4−CN−5−S(O)2CF3−2−Py]、[1390:6−CN−5−S(O)2CF3−2−Py]、[1391:3−OMe−5−S(O)2CF3−2−Py]、[1392:4−OMe−5−S(O)2CF3−2−Py]、[1393:6−OMe−5−S(O)2CF3−2−Py]、[1394:6−S(O)2CF3−2−Py]、[1395:3−Cl−6−S(O)2CF3−2−Py]、[1396:4−Cl−6−S(O)2CF3−2−Py]、[1397:5−Cl−6−S(O)2CF3−2−Py]、[1398:3−Me−6−S(O)2CF3−2−Py]、[1399:4−Me−6−S(O)2CF3−2−Py]、[1400:5−Me−6−S(O)2CF3−2−Py]、 [1301: 6-Cl-4-S (O) 2Me-2-Py], [1302: 3-Me-4-S (O) 2Me-2-Py], [1303: 5-Me-4-S (O) 2Me-2-Py], [1304: 6-Me-4-S (O) 2Me-2-Py], [1305: 3-CF3-4-S (O) 2Me-2-Py], [1306: 5-CF3-4-S (O) 2Me-2-Py], [1307: 6-CF3-4-S (O) 2Me-2-Py], [1308: 3-CN-4-S (O) 2Me-2-Py], [1309: 5-CN-4-S (O) 2Me-2-Py], [1310: 6-CN-4-S (O) 2Me-2-Py], [1311: 3-OMe-4-S (O) 2Me-2-Py], [1312: 5-OMe-4-S (O) 2Me-2-Py], [131 : 6-OMe-4-S (O) 2Me-2-Py], [1314: 5-S (O) 2Me-2-Py], [1315: 3-Cl-5-S (O) 2Me-2 -Py], [1316: 4-Cl-5-S (O) 2Me-2-Py], [1317: 6-Cl-5-S (O) 2Me-2-Py], [1318: 3-Me -5-S (O) 2Me-2-Py], [1319: 4-Me-5-S (O) 2Me-2-Py], [1320: 6-Me-5-S (O) 2Me-2. -Py], [1321: 3-CF3-5-S (O) 2Me-2-Py], [1322: 4-CF3-5-S (O) 2Me-2-Py], [1323: 6-CF3 -5-S (O) 2Me-2-Py], [1324: 3-CN-5-S (O) 2Me-2-Py], [1325: 4-CN-5-S. O) 2Me-2-Py], [1326: 6-CN-5-S (O) 2Me-2-Py], [1327: 3-OMe-5-S (O) 2Me-2-Py], [ 1328: 4-OMe-5-S (O) 2Me-2-Py], [1329: 6-OMe-5-S (O) 2Me-2-Py], [1330: 6-S (O) 2Me- 2-Py], [1331: 3-Cl-6-S (O) 2Me-2-Py], [1332: 4-Cl-6-S (O) 2Me-2-Py], [1333: 5- Cl-6-S (O) 2Me-2-Py], [1334: 3-Me-6-S (O) 2Me-2-Py], [1335: 4-Me-6-S (O) 2Me- 2-Py], [1336: 5-Me-6-S (O) 2Me-2-Py], [1337: 3-CF3-6-S (O) 2Me-2-Py ], [1338: 4-CF3-6-S (O) 2Me-2-Py], [1339: 5-CF3-6-S (O) 2Me-2-Py], [1340: 3-CN-6 -S (O) 2Me-2-Py], [1341: 4-CN-6-S (O) 2Me-2-Py], [1342: 5-CN-6-S (O) 2Me-2-Py ], [1343: 3-OMe-6-S (O) 2Me-2-Py], [1344: 4-OMe-6-S (O) 2Me-2-Py], [1345: 5-OMe-6 -S (O) 2Me-2-Py], [1346: 3-S (O) 2CF3-2-Py], [1347: 4-Cl-3-S (O) 2CF3-2-Py], [1348 : 5-Cl-3-S (O) 2CF3-2-Py], [1349: 6-Cl-3-S (O) 2CF3-2-Py], [13 0: 4-Me-3-S (O) 2CF3-2-Py], [1351: 5-Me-3-S (O) 2CF3-2-Py], [1352: 6-Me-3-S ( O) 2CF3-2-Py], [1353: 4-CF3-3-S (O) 2CF3-2-Py], [1354: 5-CF3-3-S (O) 2CF3-2-Py], [ 1355: 6-CF3-3-S (O) 2CF3-2-Py], [1356: 4-CN-3-S (O) 2CF3-2-Py], [1357: 5-CN-3-S ( O) 2CF3-2-Py], [1358: 6-CN-3-S (O) 2CF3-2-Py], [1359: 4-OMe-3-S (O) 2CF3-2-Py], [ 1360: 5-OMe-3-S (O) 2CF3-2-Py], [1361: 6-OMe-3-S (O) 2CF3- -Py], [1362: 4-S (O) 2CF3-2-Py], [1363: 3-Cl-4-S (O) 2CF3-2-Py], [1364: 5-Cl-4-S. (O) 2CF3-2-Py], [1365: 6-Cl-4-S (O) 2CF3-2-Py], [1366: 3-Me-4-S (O) 2CF3-2-Py], [1367: 5-Me-4-S (O) 2CF3-2-Py], [1368: 6-Me-4-S (O) 2CF3-2-Py], [1369: 3-CF3-4-S (O) 2CF3-2-Py], [1370: 5-CF3-4-S (O) 2CF3-2-Py], [1371: 6-CF3-4-S (O) 2CF3-2-Py], [1372: 3-CN-4-S (O) 2CF3-2-Py], [1373: 5-CN-4-S (O) 2CF3- 2-Py], [1374: 6-CN-4-S (O) 2CF3-2-Py], [1375: 3-OMe-4-S (O) 2CF3-2-Py], [1376: 5- OMe-4-S (O) 2CF3-2-Py], [1377: 6-OMe-4-S (O) 2CF3-2-Py], [1378: 5-S (O) 2CF3-2-Py] [1379: 3-Cl-5-S (O) 2CF3-2-Py], [1380: 4-Cl-5-S (O) 2CF3-2-Py], [1381: 6-Cl-5- S (O) 2CF3-2-Py], [1382: 3-Me-5-S (O) 2CF3-2-Py], [1383: 4-Me-5-S (O) 2CF3-2-Py] [1384: 6-Me-5-S (O) 2CF3-2-Py], [1385: 3-CF3-5-S (O) 2CF -2-Py], [1386: 4-CF3-5-S (O) 2CF3-2-Py], [1387: 6-CF3-5-S (O) 2CF3-2-Py], [1388: 3 -CN-5-S (O) 2CF3-2-Py], [1389: 4-CN-5-S (O) 2CF3-2-Py], [1390: 6-CN-5-S (O) 2CF3 -2-Py], [1391: 3-OMe-5-S (O) 2CF3-2-Py], [1392: 4-OMe-5-S (O) 2CF3-2-Py], [1393: 6 -OMe-5-S (O) 2CF3-2-Py], [1394: 6-S (O) 2CF3-2-Py], [1395: 3-Cl-6-S (O) 2CF3-2-Py ], [1396: 4-Cl-6-S (O) 2CF3-2-Py], [1397: 5-Cl-6-S (O) CF3-2-Py], [1398: 3-Me-6-S (O) 2CF3-2-Py], [1399: 4-Me-6-S (O) 2CF3-2-Py], [1400: 5-Me-6-S (O) 2CF3-2-Py],
[1401:3−CF3−6−S(O)2CF3−2−Py]、[1402:4−CF3−6−S(O)2CF3−2−Py]、[1403:5−CF3−6−S(O)2CF3−2−Py]、[1404:3−CN−6−S(O)2CF3−2−Py]、[1405:4−CN−6−S(O)2CF3−2−Py]、[1406:5−CN−6−S(O)2CF3−2−Py]、[1407:3−OMe−6−S(O)2CF3−2−Py]、[1408:4−OMe−6−S(O)2CF3−2−Py]、[1409:5−OMe−6−S(O)2CF3−2−Py]、[1410:3−CN−2−Py]、[1411:4−Cl−3−CN−2−Py]、[1412:5−Cl−3−CN−2−Py]、[1413:6−Cl−3−CN−2−Py]、[1414:4−Me−3−CN−2−Py]、[1415:5−Me−3−CN−2−Py]、[1416:6−Me−3−CN−2−Py]、[1417:4−CF3−3−CN−2−Py]、[1418:5−CF3−3−CN−2−Py]、[1419:6−CF3−3−CN−2−Py]、[1420:4−CN−3−CN−2−Py]、[1421:5−CN−3−CN−2−Py]、[1422:6−CN−3−CN−2−Py]、[1423:4−OMe−3−CN−2−Py]、[1424:5−OMe−3−CN−2−Py]、[1425:6−OMe−3−CN−2−Py]、[1426:4−CN−2−Py]、[1427:3−Cl−4−CN−2−Py]、[1428:5−Cl−4−CN−2−Py]、[1429:6−Cl−4−CN−2−Py]、[1430:3−Me−4−CN−2−Py]、[1431:5−Me−4−CN−2−Py]、[1432:6−Me−4−CN−2−Py]、[1433:3−CF3−4−CN−2−Py]、[1434:5−CF3−4−CN−2−Py]、[1435:6−CF3−4−CN−2−Py]、[1436:3−CN−4−CN−2−Py]、[1437:5−CN−4−CN−2−Py]、[1438:6−CN−4−CN−2−Py]、[1439:3−OMe−4−CN−2−Py]、[1440:5−OMe−4−CN−2−Py]、[1441:6−OMe−4−CN−2−Py]、[1442:5−CN−2−Py]、[1443:3−Cl−5−CN−2−Py]、[1444:4−Cl−5−CN−2−Py]、[1445:6−Cl−5−CN−2−Py]、[1446:3−Me−5−CN−2−Py]、[1447:4−Me−5−CN−2−Py]、[1448:6−Me−5−CN−2−Py]、[1449:3−CF3−5−CN−2−Py]、[1450:4−CF3−5−CN−2−Py]、[1451:6−CF3−5−CN−2−Py]、[1452:3−CN−5−CN−2−Py]、[1453:4−CN−5−CN−2−Py]、[1454:6−CN−5−CN−2−Py]、[1455:3−OMe−5−CN−2−Py]、[1456:4−OMe−5−CN−2−Py]、[1457:6−OMe−5−CN−2−Py]、[1458:6−CN−2−Py]、[1459:3−Cl−6−CN−2−Py]、[1460:4−Cl−6−CN−2−Py]、[1461:5−Cl−6−CN−2−Py]、[1462:3−Me−6−CN−2−Py]、[1463:4−Me−6−CN−2−Py]、[1464:5−Me−6−CN−2−Py]、[1465:3−CF3−6−CN−2−Py]、[1466:4−CF3−6−CN−2−Py]、[1467:5−CF3−6−CN−2−Py]、[1468:3−CN−6−CN−2−Py]、[1469:4−CN−6−CN−2−Py]、[1470:5−CN−6−CN−2−Py]、[1471:3−OMe−6−CN−2−Py]、[1472:4−OMe−6−CN−2−Py]、[1473:5−OMe−6−CN−2−Py]、[1474:3−COOMe−2−Py]、[1475:4−Cl−3−COOMe−2−Py]、[1476:5−Cl−3−COOMe−2−Py]、[1477:6−Cl−3−COOMe−2−Py]、[1478:4−Me−3−COOMe−2−Py]、[1479:5−Me−3−COOMe−2−Py]、[1480:6−Me−3−COOMe−2−Py]、[1481:4−CF3−3−COOMe−2−Py]、[1482:5−CF3−3−COOMe−2−Py]、[1483:6−CF3−3−COOMe−2−Py]、[1484:4−CN−3−COOMe−2−Py]、[1485:5−CN−3−COOMe−2−Py]、[1486:6−CN−3−COOMe−2−Py]、[1487:4−OMe−3−COOMe−2−Py]、[1488:5−OMe−3−COOMe−2−Py]、[1489:6−OMe−3−COOMe−2−Py]、[1490:4−COOMe−2−Py]、[1491:3−Cl−4−COOMe−2−Py]、[1492:5−Cl−4−COOMe−2−Py]、[1493:6−Cl−4−COOMe−2−Py]、[1494:3−Me−4−COOMe−2−Py]、[1495:5−Me−4−COOMe−2−Py]、[1496:6−Me−4−COOMe−2−Py]、[1497:3−CF3−4−COOMe−2−Py]、[1498:5−CF3−4−COOMe−2−Py]、[1499:6−CF3−4−COOMe−2−Py]、[1500:3−CN−4−COOMe−2−Py]、 [1401: 3-CF3-6-S (O) 2CF3-2-Py], [1402: 4-CF3-6-S (O) 2CF3-2-Py], [1403: 5-CF3-6-S (O) 2CF3-2-Py], [1404: 3-CN-6-S (O) 2CF3-2-Py], [1405: 4-CN-6-S (O) 2CF3-2-Py], [1406: 5-CN-6-S (O) 2CF3-2-Py], [1407: 3-OMe-6-S (O) 2CF3-2-Py], [1408: 4-OMe-6-S (O) 2CF3-2-Py], [1409: 5-OMe-6-S (O) 2CF3-2-Py], [1410: 3-CN-2-Py], [1411: 4-Cl-3 -CN-2-Py], [1412: 5-Cl-3-CN-2-Py], [1413: 6-Cl-3-C -2-Py], [1414: 4-Me-3-CN-2-Py], [1415: 5-Me-3-CN-2-Py], [1416: 6-Me-3-CN-2 -Py], [1417: 4-CF3-3-CN-2-Py], [1418: 5-CF3-3-CN-2-Py], [1419: 6-CF3-3-CN-2-Py] ], [1420: 4-CN-3-CN-2-Py], [1421: 5-CN-3-CN-2-Py], [1422: 6-CN-3-CN-2-Py], [1423: 4-OMe-3-CN-2-Py], [1424: 5-OMe-3-CN-2-Py], [1425: 6-OMe-3-CN-2-Py], [1426 : 4-CN-2-Py], [1427: 3-Cl-4-CN-2-Py], [1428: 5-Cl-4-CN- -Py], [1429: 6-Cl-4-CN-2-Py], [1430: 3-Me-4-CN-2-Py], [1431: 5-Me-4-CN-2-Py ], [1432: 6-Me-4-CN-2-Py], [1433: 3-CF3-4-CN-2-Py], [1434: 5-CF3-4-CN-2-Py], [1435: 6-CF3-4-CN-2-Py], [1436: 3-CN-4-CN-2-Py], [1437: 5-CN-4-CN-2-Py], [1438 : 6-CN-4-CN-2-Py], [1439: 3-OMe-4-CN-2-Py], [1440: 5-OMe-4-CN-2-Py], [1441: 6 -OMe-4-CN-2-Py], [1442: 5-CN-2-Py], [1443: 3-Cl-5-CN-2-P y], [1444: 4-Cl-5-CN-2-Py], [1445: 6-Cl-5-CN-2-Py], [1446: 3-Me-5-CN-2-Py] [1447: 4-Me-5-CN-2-Py], [1448: 6-Me-5-CN-2-Py], [1449: 3-CF3-5-CN-2-Py], [ 1450: 4-CF3-5-CN-2-Py], [1451: 6-CF3-5-CN-2-Py], [1452: 3-CN-5-CN-2-Py], [1453: 4-CN-5-CN-2-Py], [1454: 6-CN-5-CN-2-Py], [1455: 3-OMe-5-CN-2-Py], [1456: 4- OMe-5-CN-2-Py], [1457: 6-OMe-5-CN-2-Py], [1458: 6-CN-2-Py] [1458: 3-Cl-6-CN-2-Py], [1460: 4-Cl-6-CN-2-Py], [1461: 5-Cl-6-CN-2-Py], [1462 : 3-Me-6-CN-2-Py], [1463: 4-Me-6-CN-2-Py], [1464: 5-Me-6-CN-2-Py], [1465: 3 -CF3-6-CN-2-Py], [1466: 4-CF3-6-CN-2-Py], [1467: 5-CF3-6-CN-2-Py], [1468: 3-CN -6-CN-2-Py], [1469: 4-CN-6-CN-2-Py], [1470: 5-CN-6-CN-2-Py], [1471: 3-OMe-6 -CN-2-Py], [1472: 4-OMe-6-CN-2-Py], [1473: 5-OMe-6-CN-2- y], [1474: 3-COOMe-2-Py], [1475: 4-Cl-3-COOMe-2-Py], [1476: 5-Cl-3-COOMe-2-Py], [1477: 6-Cl-3-COOMe-2-Py], [1478: 4-Me-3-COOMe-2-Py], [1479: 5-Me-3-COOMe-2-Py], [1480: 6- Me-3-COOMe-2-Py], [1481: 4-CF3-3-COOMe-2-Py], [1482: 5-CF3-3-COOMe-2-Py], [1483: 6-CF3- 3-COOMe-2-Py], [1484: 4-CN-3-COOMe-2-Py], [1485: 5-CN-3-COOMe-2-Py], [1486: 6-CN-3- COOMe-2-Py], [1487: 4 -OMe-3-COOMe-2-Py], [1488: 5-OMe-3-COOMe-2-Py], [1489: 6-OMe-3-COOMe-2-Py], [1490: 4-COOMe -2-Py], [1491: 3-Cl-4-COOMe-2-Py], [1492: 5-Cl-4-COOMe-2-Py], [1493: 6-Cl-4-COOMe-2 -Py], [1494: 3-Me-4-COOMe-2-Py], [1495: 5-Me-4-COOMe-2-Py], [1496: 6-Me-4-COOMe-2-Py] ], [1497: 3-CF3-4-COOMe-2-Py], [1498: 5-CF3-4-COOMe-2-Py], [1499: 6-CF3-4-COOMe-2-Py], [1500: 3-CN-4-C OMe-2-Py],
[1501:5−CN−4−COOMe−2−Py]、[1502:6−CN−4−COOMe−2−Py]、[1503:3−OMe−4−COOMe−2−Py]、[1504:5−OMe−4−COOMe−2−Py]、[1505:6−OMe−4−COOMe−2−Py]、[1506:5−COOMe−2−Py]、[1507:3−Cl−5−COOMe−2−Py]、[1508:4−Cl−5−COOMe−2−Py]、[1509:6−Cl−5−COOMe−2−Py]、[1510:3−Me−5−COOMe−2−Py]、[1511:4−Me−5−COOMe−2−Py]、[1512:6−Me−5−COOMe−2−Py]、[1513:3−CF3−5−COOMe−2−Py]、[1514:4−CF3−5−COOMe−2−Py]、[1515:6−CF3−5−COOMe−2−Py]、[1516:3−CN−5−COOMe−2−Py]、[1517:4−CN−5−COOMe−2−Py]、[1518:6−CN−5−COOMe−2−Py]、[1519:3−OMe−5−COOMe−2−Py]、[1520:4−OMe−5−COOMe−2−Py]、[1521:6−OMe−5−COOMe−2−Py]、[1522:6−COOMe−2−Py]、[1523:3−Cl−6−COOMe−2−Py]、[1524:4−Cl−6−COOMe−2−Py]、[1525:5−Cl−6−COOMe−2−Py]、[1526:3−Me−6−COOMe−2−Py]、[1527:4−Me−6−COOMe−2−Py]、[1528:5−Me−6−COOMe−2−Py]、[1529:3−CF3−6−COOMe−2−Py]、[1530:4−CF3−6−COOMe−2−Py]、[1531:5−CF3−6−COOMe−2−Py]、[1532:3−CN−6−COOMe−2−Py]、[1533:4−CN−6−COOMe−2−Py]、[1534:5−CN−6−COOMe−2−Py]、[1535:3−OMe−6−COOMe−2−Py]、[1536:4−OMe−6−COOMe−2−Py]、[1537:5−OMe−6−COOMe−2−Py]、[1538:3−NO2−2−Py]、[1539:4−Cl−3−NO2−2−Py]、[1540:5−Cl−3−NO2−2−Py]、[1541:6−Cl−3−NO2−2−Py]、[1542:4−Me−3−NO2−2−Py]、[1543:5−Me−3−NO2−2−Py]、[1544:6−Me−3−NO2−2−Py]、[1545:4−CF3−3−NO2−2−Py]、[1546:5−CF3−3−NO2−2−Py]、[1547:6−CF3−3−NO2−2−Py]、[1548:4−CN−3−NO2−2−Py]、[1549:5−CN−3−NO2−2−Py]、[1550:6−CN−3−NO2−2−Py]、[1551:4−OMe−3−NO2−2−Py]、[1552:5−OMe−3−NO2−2−Py]、[1553:6−OMe−3−NO2−2−Py]、[1554:4−NO2−2−Py]、[1555:3−Cl−4−NO2−2−Py]、[1556:5−Cl−4−NO2−2−Py]、[1557:6−Cl−4−NO2−2−Py]、[1558:3−Me−4−NO2−2−Py]、[1559:5−Me−4−NO2−2−Py]、[1560:6−Me−4−NO2−2−Py]、[1561:3−CF3−4−NO2−2−Py]、[1562:5−CF3−4−NO2−2−Py]、[1563:6−CF3−4−NO2−2−Py]、[1564:3−CN−4−NO2−2−Py]、[1565:5−CN−4−NO2−2−Py]、[1566:6−CN−4−NO2−2−Py]、[1567:3−OMe−4−NO2−2−Py]、[1568:5−OMe−4−NO2−2−Py]、[1569:6−OMe−4−NO2−2−Py]、[1570:5−NO2−2−Py]、[1571:3−Cl−5−NO2−2−Py]、[1572:4−Cl−5−NO2−2−Py]、[1573:6−Cl−5−NO2−2−Py]、[1574:3−Me−5−NO2−2−Py]、[1575:4−Me−5−NO2−2−Py]、[1576:6−Me−5−NO2−2−Py]、[1577:3−CF3−5−NO2−2−Py]、[1578:4−CF3−5−NO2−2−Py]、[1579:6−CF3−5−NO2−2−Py]、[1580:3−CN−5−NO2−2−Py]、[1581:4−CN−5−NO2−2−Py]、[1582:6−CN−5−NO2−2−Py]、[1583:3−OMe−5−NO2−2−Py]、[1584:4−OMe−5−NO2−2−Py]、[1585:6−OMe−5−NO2−2−Py]、[1586:6−NO2−2−Py]、[1587:3−Cl−6−NO2−2−Py]、[1588:4−Cl−6−NO2−2−Py]、[1589:5−Cl−6−NO2−2−Py]、[1590:3−Me−6−NO2−2−Py]、[1591:4−Me−6−NO2−2−Py]、[1592:5−Me−6−NO2−2−Py]、[1593:3−CF3−6−NO2−2−Py]、[1594:4−CF3−6−NO2−2−Py]、[1595:5−CF3−6−NO2−2−Py]、[1596:3−CN−6−NO2−2−Py]、[1597:4−CN−6−NO2−2−Py]、[1598:5−CN−6−NO2−2−Py]、[1599:3−OMe−6−NO2−2−Py]、[1600:4−OMe−6−NO2−2−Py]、 [1501: 5-CN-4-COOMe-2-Py], [1502: 6-CN-4-COOMe-2-Py], [1503: 3-OMe-4-COOMe-2-Py], [1504 : 5-OMe-4-COOMe-2-Py], [1505: 6-OMe-4-COOMe-2-Py], [1506: 5-COOMe-2-Py], [1507: 3-Cl-5 -COOMe-2-Py], [1508: 4-Cl-5-COOMe-2-Py], [1509: 6-Cl-5-COOMe-2-Py], [1510: 3-Me-5-COOMe -2-Py], [1511: 4-Me-5-COOMe-2-Py], [1512: 6-Me-5-COOMe-2-Py], [1513: 3-CF3-5-COOMe-2 -Py], [1514: 4-C 3-5-COOMe-2-Py], [1515: 6-CF3-5-COOMe-2-Py], [1516: 3-CN-5-COOMe-2-Py], [1517: 4-CN- 5-COOMe-2-Py], [1518: 6-CN-5-COOMe-2-Py], [1519: 3-OMe-5-COOMe-2-Py], [1520: 4-OMe-5 COOMe-2-Py], [1521: 6-OMe-5-COOMe-2-Py], [1522: 6-COOMe-2-Py], [1523: 3-Cl-6-COOMe-2-Py] [1524: 4-Cl-6-COOMe-2-Py], [1525: 5-Cl-6-COOMe-2-Py], [1526: 3-Me-6-COOMe-2-Py], [ 1527: 4-Me-6-COOM -2-Py], [1528: 5-Me-6-COOMe-2-Py], [1529: 3-CF3-6-COOMe-2-Py], [1530: 4-CF3-6-COOMe-2 -Py], [1531: 5-CF3-6-COOMe-2-Py], [1532: 3-CN-6-COOMe-2-Py], [1533: 4-CN-6-COOMe-2-Py ], [1534: 5-CN-6-COOMe-2-Py], [1535: 3-OMe-6-COOMe-2-Py], [1536: 4-OMe-6-COOMe-2-Py], [1537: 5-OMe-6-COOMe-2-Py], [1538: 3-NO2-2-2-Py], [1539: 4-Cl-3-NO2-2-2-Py], [1540: 5-Cl -3-NO2-2Py], [1541: 6-Cl-3-NO2-2-Py], [1542: 4-Me-3-NO2-2-Py], [1543: 5-Me-3-NO2-2-Py], [1544: 6- Me-3-NO2-2-2-Py], [1545: 4-CF3-3-NO2-2-Py], [1546: 5-CF3-3-NO2-2-Py], [1547: 6-CF3- 3-NO2-2-2-Py], [1548: 4-CN-3-NO2-2-2-Py], [1549: 5-CN-3-NO2-2-Py], [1550: 6-CN-3- NO2-2-2-Py], [1551: 4-OMe-3-NO2-2-2-Py], [1552: 5-OMe-3-NO2-2-2-Py], [1553: 6-OMe-3-NO2- 2-Py], [1554: 4-NO2-2-Py], [1555: 3-Cl-4-NO2 2-Py], [1556: 5-Cl-4-NO2-2-Py], [1557: 6-Cl-4-NO2-2-Py], [1558: 3-Me-4-NO2-2- Py], [1559: 5-Me-4-NO2-2-Py], [1560: 6-Me-4-NO2-2-Py], [1561: 3-CF3-4-NO2-2-Py] [1562: 5-CF3-4-NO2-2-Py], [1563: 6-CF3-4-NO2-2-2-Py], [1564: 3-CN-4-NO2-2-Py], [ 1565: 5-CN-4-NO2-2-Py], [1566: 6-CN-4-NO2-2-Py], [1567: 3-OMe-4-NO2-2-Py], [1568: 5-OMe-4-NO2-2-Py], [1569: 6-OMe-4-NO2-2-2-Py [1570: 5-NO2-2-Py], [1571: 3-Cl-5-NO2-2-2-Py], [1572: 4-Cl-5-NO2-2-Py], [1573: 6- Cl-5-NO2-2-2-Py], [1574: 3-Me-5-NO2-2-2-Py], [1575: 4-Me-5-NO2-2-Py], [1576: 6-Me- 5-NO2-2-2-Py], [1577: 3-CF3-5-NO2-2-2-Py], [1578: 4-CF3-5-NO2-2-2-Py], [1579: 6-CF3-5 NO2-2-2-Py], [1580: 3-CN-5-NO2-2-2-Py], [1581: 4-CN-5-NO2-2-2-Py], [1582: 6-CN-5-NO2- 2-Py], [1583: 3-OMe-5-NO2-2-Py], [1584: 4-OMe -5-NO2-2-Py], [1585: 6-OMe-5-NO2-2-Py], [1586: 6-NO2-2-Py], [1587: 3-Cl-6-NO2-2 -Py], [1588: 4-Cl-6-NO2-2-Py], [1589: 5-Cl-6-NO2-2-Py], [1590: 3-Me-6-NO2-2-Py ], [1591: 4-Me-6-NO2-2-Py], [1592: 5-Me-6-NO2-2-Py], [1593: 3-CF3-6-NO2-2-Py], [1594: 4-CF3-6-NO2-2-Py], [1595: 5-CF3-6-NO2-2-Py], [1596: 3-CN-6-NO2-2-Py], [1597 : 4-CN-6-NO2-2-Py], [1598: 5-CN-6-NO2-2-Py] [1599: 3-OMe-6-NO2-2-Py], [1600: 4-OMe-6-NO2-2-Py],
[1601:5−OMe−6−NO2−2−Py]、[1602:3−NH2−2−Py]、[1603:4−Cl−3−NH2−2−Py]、[1604:5−Cl−3−NH2−2−Py]、[1605:6−Cl−3−NH2−2−Py]、[1606:4−Me−3−NH2−2−Py]、[1607:5−Me−3−NH2−2−Py]、[1608:6−Me−3−NH2−2−Py]、[1609:4−CF3−3−NH2−2−Py]、[1610:5−CF3−3−NH2−2−Py]、[1611:6−CF3−3−NH2−2−Py]、[1612:4−CN−3−NH2−2−Py]、[1613:5−CN−3−NH2−2−Py]、[1614:6−CN−3−NH2−2−Py]、[1615:4−OMe−3−NH2−2−Py]、[1616:5−OMe−3−NH2−2−Py]、[1617:6−OMe−3−NH2−2−Py]、[1618:4−NH2−2−Py]、[1619:3−Cl−4−NH2−2−Py]、[1620:5−Cl−4−NH2−2−Py]、[1621:6−Cl−4−NH2−2−Py]、[1622:3−Me−4−NH2−2−Py]、[1623:5−Me−4−NH2−2−Py]、[1624:6−Me−4−NH2−2−Py]、[1625:3−CF3−4−NH2−2−Py]、[1626:5−CF3−4−NH2−2−Py]、[1627:6−CF3−4−NH2−2−Py]、[1628:3−CN−4−NH2−2−Py]、[1629:5−CN−4−NH2−2−Py]、[1630:6−CN−4−NH2−2−Py]、[1631:3−OMe−4−NH2−2−Py]、[1632:5−OMe−4−NH2−2−Py]、[1633:6−OMe−4−NH2−2−Py]、[1634:5−NH2−2−Py]、[1635:3−Cl−5−NH2−2−Py]、[1636:4−Cl−5−NH2−2−Py]、[1637:6−Cl−5−NH2−2−Py]、[1638:3−Me−5−NH2−2−Py]、[1639:4−Me−5−NH2−2−Py]、[1640:6−Me−5−NH2−2−Py]、[1641:3−CF3−5−NH2−2−Py]、[1642:4−CF3−5−NH2−2−Py]、[1643:6−CF3−5−NH2−2−Py]、[1644:3−CN−5−NH2−2−Py]、[1645:4−CN−5−NH2−2−Py]、[1646:6−CN−5−NH2−2−Py]、[1647:3−OMe−5−NH2−2−Py]、[1648:4−OMe−5−NH2−2−Py]、[1649:6−OMe−5−NH2−2−Py]、[1650:6−NH2−2−Py]、[1651:3−Cl−6−NH2−2−Py]、[1652:4−Cl−6−NH2−2−Py]、[1653:5−Cl−6−NH2−2−Py]、[1654:3−Me−6−NH2−2−Py]、[1655:4−Me−6−NH2−2−Py]、[1656:5−Me−6−NH2−2−Py]、[1657:3−CF3−6−NH2−2−Py]、[1658:4−CF3−6−NH2−2−Py]、[1659:5−CF3−6−NH2−2−Py]、[1660:3−CN−6−NH2−2−Py]、[1661:4−CN−6−NH2−2−Py]、[1662:5−CN−6−NH2−2−Py]、[1663:3−OMe−6−NH2−2−Py]、[1664:4−OMe−6−NH2−2−Py]、[1665:5−OMe−6−NH2−2−Py]、[1666:3−NHMe−2−Py]、[1667:4−Cl−3−NHMe−2−Py]、[1668:5−Cl−3−NHMe−2−Py]、[1669:6−Cl−3−NHMe−2−Py]、[1670:4−Me−3−NHMe−2−Py]、[1671:5−Me−3−NHMe−2−Py]、[1672:6−Me−3−NHMe−2−Py]、[1673:4−CF3−3−NHMe−2−Py]、[1674:5−CF3−3−NHMe−2−Py]、[1675:6−CF3−3−NHMe−2−Py]、[1676:4−CN−3−NHMe−2−Py]、[1677:5−CN−3−NHMe−2−Py]、[1678:6−CN−3−NHMe−2−Py]、[1679:4−OMe−3−NHMe−2−Py]、[1680:5−OMe−3−NHMe−2−Py]、[1681:6−OMe−3−NHMe−2−Py]、[1682:4−NHMe−2−Py]、[1683:3−Cl−4−NHMe−2−Py]、[1684:5−Cl−4−NHMe−2−Py]、[1685:6−Cl−4−NHMe−2−Py]、[1686:3−Me−4−NHMe−2−Py]、[1687:5−Me−4−NHMe−2−Py]、[1688:6−Me−4−NHMe−2−Py]、[1689:3−CF3−4−NHMe−2−Py]、[1690:5−CF3−4−NHMe−2−Py]、[1691:6−CF3−4−NHMe−2−Py]、[1692:3−CN−4−NHMe−2−Py]、[1693:5−CN−4−NHMe−2−Py]、[1694:6−CN−4−NHMe−2−Py]、[1695:3−OMe−4−NHMe−2−Py]、[1696:5−OMe−4−NHMe−2−Py]、[1697:6−OMe−4−NHMe−2−Py]、[1698:5−NHMe−2−Py]、[1699:3−Cl−5−NHMe−2−Py]、[1700:4−Cl−5−NHMe−2−Py]、 [1601: 5-OMe-6-NO2-2-Py], [1602: 3-NH2-2-Py], [1603: 4-Cl-3-NH2-2-Py], [1604: 5-Cl -3-NH2-2-Py], [1605: 6-Cl-3-NH2-2-Py], [1606: 4-Me-3-NH2-2-Py], [1607: 5-Me-3 -NH2-2-Py], [1608: 6-Me-3-NH2-2-Py], [1609: 4-CF3-3-NH2-2-Py], [1610: 5-CF3-3-NH2 -2-Py], [1611: 6-CF3-3-NH2-2-Py], [1612: 4-CN-3-NH2-2-Py], [1613: 5-CN-3-NH2-2 -Py], [1614: 6-CN-3-NH2-2-Py], [1615: 4-OMe- -NH2-2-Py], [1616: 5-OMe-3-NH2-2-Py], [1617: 6-OMe-3-NH2-2-Py], [1618: 4-NH2-2-Py] ], [1619: 3-Cl-4-NH2-2-Py], [1620: 5-Cl-4-NH2-2-Py], [1621: 6-Cl-4-NH2-2-Py], [1622: 3-Me-4-NH2-2-Py], [1623: 5-Me-4-NH2-2-Py], [1624: 6-Me-4-NH2-2-Py], [1625 : 3-CF3-4-NH2-2-Py], [1626: 5-CF3-4-NH2-2-Py], [1627: 6-CF3-4-NH2-2-Py], [1628: 3 -CN-4-NH2-2-Py], [1629: 5-CN-4-NH2-2-Py] [1630: 6-CN-4-NH2-2-Py], [1631: 3-OMe-4-NH2-2-Py], [1632: 5-OMe-4-NH2-2-Py], [1633 : 6-OMe-4-NH2-2-Py], [1634: 5-NH2-2-Py], [1635: 3-Cl-5-NH2-2-Py], [1636: 4-Cl-5 -NH2-2-Py], [1637: 6-Cl-5-NH2-2-Py], [1638: 3-Me-5-NH2-2-Py], [1639: 4-Me-5-NH2 -2-Py], [1640: 6-Me-5-NH2-2-Py], [1641: 3-CF3-5-NH2-2-Py], [1642: 4-CF3-5-NH2-2 -Py], [1643: 6-CF3-5-NH2-2-Py], [1644: 3-CN -5-NH2-2-Py], [1645: 4-CN-5-NH2-2-Py], [1646: 6-CN-5-NH2-2-Py], [1647: 3-OMe-5 -NH2-2-Py], [1648: 4-OMe-5-NH2-2-Py], [1649: 6-OMe-5-NH2-2-Py], [1650: 6-NH2-2-Py] ], [1651: 3-Cl-6-NH2-2-Py], [1652: 4-Cl-6-NH2-2-Py], [1653: 5-Cl-6-NH2-2-Py], [1654: 3-Me-6-NH2-2-Py], [1655: 4-Me-6-NH2-2-Py], [1656: 5-Me-6-NH2-2-Py], [1657 : 3-CF3-6-NH2-2-Py], [1658: 4-CF3-6-NH2-2-Py [1659: 5-CF3-6-NH2-2-Py], [1660: 3-CN-6-NH2-2-Py], [1661: 4-CN-6-NH2-2-Py], [ 1662: 5-CN-6-NH2-2-Py], [1663: 3-OMe-6-NH2-2-Py], [1664: 4-OMe-6-NH2-2-Py], [1665: 5-OMe-6-NH2-2-Py], [1666: 3-NHMe-2-Py], [1667: 4-Cl-3-NHMe-2-Py], [1668: 5-Cl-3- NHMe-2-Py], [1669: 6-Cl-3-NHMe-2-Py], [1670: 4-Me-3-NHMe-2-Py], [1671: 5-Me-3-NHMe- 2-Py], [1672: 6-Me-3-NHMe-2-Py], [16 3: 4-CF3-3-NHMe-2-Py], [1674: 5-CF3-3-NHMe-2-Py], [1675: 6-CF3-3-NHMe-2-Py], [1676: 4-CN-3-NHMe-2-Py], [1679: 5-CN-3-NHMe-2-Py], [1678: 6-CN-3-NHMe-2-Py], [1679: 4- OMe-3-NHMe-2-Py], [1680: 5-OMe-3-NHMe-2-Py], [1681: 6-OMe-3-NHMe-2-Py], [1682: 4-NHMe- 2-Py], [1683: 3-Cl-4-NHMe-2-Py], [1684: 5-Cl-4-NHMe-2-Py], [1685: 6-Cl-4-NHMe-2- Py], [1686: 3-Me-4-NHMe-2-Py], [1687: 5-Me-4-NHMe-2-Py], [1688: 6-Me-4-NHMe-2-Py], [1689: 3-CF3-4-NHMe-2-Py], [1690 : 5-CF3-4-NHMe-2-Py], [1691: 6-CF3-4-NHMe-2-Py], [1692: 3-CN-4-NHMe-2-Py], [1693: 5 -CN-4-NHMe-2-Py], [1694: 6-CN-4-NHMe-2-Py], [1695: 3-OMe-4-NHMe-2-Py], [1696: 5-OMe -4-NHMe-2-Py], [1697: 6-OMe-4-NHMe-2-Py], [1698: 5-NHMe-2-Py], [1699: 3-Cl-5-NHMe-2 -Py], [1700: 4-Cl-5-NHMe-2- y],
[1701:6−Cl−5−NHMe−2−Py]、[1702:3−Me−5−NHMe−2−Py]、[1703:4−Me−5−NHMe−2−Py]、[1704:6−Me−5−NHMe−2−Py]、[1705:3−CF3−5−NHMe−2−Py]、[1706:4−CF3−5−NHMe−2−Py]、[1707:6−CF3−5−NHMe−2−Py]、[1708:3−CN−5−NHMe−2−Py]、[1709:4−CN−5−NHMe−2−Py]、[1710:6−CN−5−NHMe−2−Py]、[1711:3−OMe−5−NHMe−2−Py]、[1712:4−OMe−5−NHMe−2−Py]、[1713:6−OMe−5−NHMe−2−Py]、[1714:6−NHMe−2−Py]、[1715:3−Cl−6−NHMe−2−Py]、[1716:4−Cl−6−NHMe−2−Py]、[1717:5−Cl−6−NHMe−2−Py]、[1718:3−Me−6−NHMe−2−Py]、[1719:4−Me−6−NHMe−2−Py]、[1720:5−Me−6−NHMe−2−Py]、[1721:3−CF3−6−NHMe−2−Py]、[1722:4−CF3−6−NHMe−2−Py]、[1723:5−CF3−6−NHMe−2−Py]、[1724:3−CN−6−NHMe−2−Py]、[1725:4−CN−6−NHMe−2−Py]、[1726:5−CN−6−NHMe−2−Py]、[1727:3−OMe−6−NHMe−2−Py]、[1728:4−OMe−6−NHMe−2−Py]、[1729:5−OMe−6−NHMe−2−Py]、[1730:3−NMe2−2−Py]、[1731:4−Cl−3−NMe2−2−Py]、[1732:5−Cl−3−NMe2−2−Py]、[1733:6−Cl−3−NMe2−2−Py]、[1734:4−Me−3−NMe2−2−Py]、[1735:5−Me−3−NMe2−2−Py]、[1736:6−Me−3−NMe2−2−Py]、[1737:4−CF3−3−NMe2−2−Py]、[1738:5−CF3−3−NMe2−2−Py]、[1739:6−CF3−3−NMe2−2−Py]、[1740:4−CN−3−NMe2−2−Py]、[1741:5−CN−3−NMe2−2−Py]、[1742:6−CN−3−NMe2−2−Py]、[1743:4−OMe−3−NMe2−2−Py]、[1744:5−OMe−3−NMe2−2−Py]、[1745:6−OMe−3−NMe2−2−Py]、[1746:4−NMe2−2−Py]、[1747:3−Cl−4−NMe2−2−Py]、[1748:5−Cl−4−NMe2−2−Py]、[1749:6−Cl−4−NMe2−2−Py]、[1750:3−Me−4−NMe2−2−Py]、[1751:5−Me−4−NMe2−2−Py]、[1752:6−Me−4−NMe2−2−Py]、[1753:3−CF3−4−NMe2−2−Py]、[1754:5−CF3−4−NMe2−2−Py]、[1755:6−CF3−4−NMe2−2−Py]、[1756:3−CN−4−NMe2−2−Py]、[1757:5−CN−4−NMe2−2−Py]、[1758:6−CN−4−NMe2−2−Py]、[1759:3−OMe−4−NMe2−2−Py]、[1760:5−OMe−4−NMe2−2−Py]、[1761:6−OMe−4−NMe2−2−Py]、[1762:5−NMe2−2−Py]、[1763:3−Cl−5−NMe2−2−Py]、[1764:4−Cl−5−NMe2−2−Py]、[1765:6−Cl−5−NMe2−2−Py]、[1766:3−Me−5−NMe2−2−Py]、[1767:4−Me−5−NMe2−2−Py]、[1768:6−Me−5−NMe2−2−Py]、[1769:3−CF3−5−NMe2−2−Py]、[1770:4−CF3−5−NMe2−2−Py]、[1771:6−CF3−5−NMe2−2−Py]、[1772:3−CN−5−NMe2−2−Py]、[1773:4−CN−5−NMe2−2−Py]、[1774:6−CN−5−NMe2−2−Py]、[1775:3−OMe−5−NMe2−2−Py]、[1776:4−OMe−5−NMe2−2−Py]、[1777:6−OMe−5−NMe2−2−Py]、[1778:6−NMe2−2−Py]、[1779:3−Cl−6−NMe2−2−Py]、[1780:4−Cl−6−NMe2−2−Py]、[1781:5−Cl−6−NMe2−2−Py]、[1782:3−Me−6−NMe2−2−Py]、[1783:4−Me−6−NMe2−2−Py]、[1784:5−Me−6−NMe2−2−Py]、[1785:3−CF3−6−NMe2−2−Py]、[1786:4−CF3−6−NMe2−2−Py]、[1787:5−CF3−6−NMe2−2−Py]、[1788:3−CN−6−NMe2−2−Py]、[1789:4−CN−6−NMe2−2−Py]、[1790:5−CN−6−NMe2−2−Py]、[1791:3−OMe−6−NMe2−2−Py]、[1792:4−OMe−6−NMe2−2−Py]、[1793:5−OMe−6−NMe2−2−Py]、[1794:3−ACNH−2−Py]、[1795:4−Cl−3−ACNH−2−Py]、[1796:5−Cl−3−ACNH−2−Py]、[1797:6−Cl−3−ACNH−2−Py]、[1798:4−Me−3−ACNH−2−Py]、[1799:5−Me−3−ACNH−2−Py]、[1800:6−Me−3−ACNH−2−Py]、 [1701: 6-Cl-5-NHMe-2-Py], [1702: 3-Me-5-NHMe-2-Py], [1703: 4-Me-5-NHMe-2-Py], [1704 : 6-Me-5-NHMe-2-Py], [1705: 3-CF3-5-NHMe-2-Py], [1706: 4-CF3-5-NHMe-2-Py], [1707: 6 -CF3-5-NHMe-2-Py], [1708: 3-CN-5-NHMe-2-Py], [1709: 4-CN-5-NHMe-2-Py], [1710: 6-CN -5-NHMe-2-Py], [1711: 3-OMe-5-NHMe-2-Py], [1712: 4-OMe-5-NHMe-2-Py], [1713: 6-OMe-5 -NHMe-2-Py], [1714: 6-NHMe-2- y], [1715: 3-Cl-6-NHMe-2-Py], [1716: 4-Cl-6-NHMe-2-Py], [1717: 5-Cl-6-NHMe-2-Py] [1718: 3-Me-6-NHMe-2-Py], [1719: 4-Me-6-NHMe-2-Py], [1720: 5-Me-6-NHMe-2-Py], [ 1721: 3-CF3-6-NHMe-2-Py], [1722: 4-CF3-6-NHMe-2-Py], [1723: 5-CF3-6-NHMe-2-Py], [1724: 3-CN-6-NHMe-2-Py], [1725: 4-CN-6-NHMe-2-Py], [1726: 5-CN-6-NHMe-2-Py], [1727: 3- OMe-6-NHMe-2-Py], [1728: 4-OMe-6 NHMe-2-Py], [1729: 5-OMe-6-NHMe-2-Py], [1730: 3-NMe2-2-Py], [1731: 4-Cl-3-NMe2-2-Py] [1732: 5-Cl-3-NMe2-2-Py], [1733: 6-Cl-3-NMe2-2-Py], [1734: 4-Me-3-NMe2-2-Py], [ 1735: 5-Me-3-NMe2-2-Py], [1736: 6-Me-3-NMe2-2-Py], [1737: 4-CF3-3-NMe2-2-Py], [1738: 5-CF3-3-NMe2-2-Py], [1739: 6-CF3-3-NMe2-2-2-Py], [1740: 4-CN-3-NMe2-2-Py], [1741: 5- CN-3-NMe2-2-Py], [1742: 6-CN- 3-NMe2-2-Py], [1743: 4-OMe-3-NMe2-2-Py], [1744: 5-OMe-3-NMe2-2-Py], [1745: 6-OMe-3- NMe2-2-Py], [1746: 4-NMe2-2-Py], [1747: 3-Cl-4-NMe2-2-Py], [1748: 5-Cl-4-NMe2-2-Py] [1749: 6-Cl-4-NMe2-2-Py], [1750: 3-Me-4-NMe2-2-Py], [1751: 5-Me-4-NMe2-2-Py], [ 1752: 6-Me-4-NMe2-2-Py], [1753: 3-CF3-4-NMe2-2-Py], [1754: 5-CF3-4-NMe2-2-Py], [1755: 6-CF3-4-NMe2-2-Py], [1756: 3 CN-4-NMe2-2-Py], [1757: 5-CN-4-NMe2-2-Py], [1758: 6-CN-4-NMe2-2-Py], [1759: 3-OMe- 4-NMe2-2-Py], [1760: 5-OMe-4-NMe2-2-Py], [1761: 6-OMe-4-NMe2-2-Py], [1762: 5-NMe2-2- Py], [1763: 3-Cl-5-NMe2-2-Py], [1764: 4-Cl-5-NMe2-2-Py], [1765: 6-Cl-5-NMe2-2-Py] [1766: 3-Me-5-NMe2-2-Py], [1767: 4-Me-5-NMe2-2-Py], [1768: 6-Me-5-NMe2-2-Py], [ 1769: 3-CF3-5-NMe2-2-2-Py], [1770 4-CF3-5-NMe2-2-Py], [1771: 6-CF3-5-NMe2-2-2-Py], [1772: 3-CN-5-NMe2-2-Py], [1773: 4- CN-5-NMe2-2-Py], [1774: 6-CN-5-NMe2-2-2-Py], [1775: 3-OMe-5-NMe2-2-Py], [1776: 4-OMe- 5-NMe2-2-Py], [1777: 6-OMe-5-NMe2-2-2-Py], [1778: 6-NMe2-2-Py], [179: 3-Cl-6-NMe2-2 Py], [1780: 4-Cl-6-NMe2-2-Py], [1781: 5-Cl-6-NMe2-2-Py], [1782: 3-Me-6-NMe2-2-Py] [1783: 4-Me-6-NMe2-2-2-Py], [17 84: 5-Me-6-NMe2-2-Py], [1785: 3-CF3-6-NMe2-2-Py], [1786: 4-CF3-6-NMe2-2-Py], [1787: 5-CF3-6-NMe2-2-Py], [1788: 3-CN-6-NMe2-2-2-Py], [1789: 4-CN-6-NMe2-2-Py], [1790: 5- CN-6-NMe2-2Py], [1791: 3-OMe-6-NMe2-2Py], [1792: 4-OMe-6-NMe2-2Py], [1793: 5-OMe- 6-NMe2-2-Py], [1794: 3-ACNH-2-Py], [1795: 4-Cl-3-ACNH-2-Py], [1796: 5-Cl-3-ACNH-2- Py], [1797: 6-Cl-3-ACNH-2-Py] [1798: 4-Me-3-ACNH-2-Py], [1799: 5-Me-3-ACNH-2-Py], [1800: 6-Me-3-ACNH-2-Py],
[1801:4−CF3−3−ACNH−2−Py]、[1802:5−CF3−3−ACNH−2−Py]、[1803:6−CF3−3−ACNH−2−Py]、[1804:4−CN−3−ACNH−2−Py]、[1805:5−CN−3−ACNH−2−Py]、[1806:6−CN−3−ACNH−2−Py]、[1807:4−OMe−3−ACNH−2−Py]、[1808:5−OMe−3−ACNH−2−Py]、[1809:6−OMe−3−ACNH−2−Py]、[1810:4−ACNH−2−Py]、[1811:3−Cl−4−ACNH−2−Py]、[1812:5−Cl−4−ACNH−2−Py]、[1813:6−Cl−4−ACNH−2−Py]、[1814:3−Me−4−ACNH−2−Py]、[1815:5−Me−4−ACNH−2−Py]、[1816:6−Me−4−ACNH−2−Py]、[1817:3−CF3−4−ACNH−2−Py]、[1818:5−CF3−4−ACNH−2−Py]、[1819:6−CF3−4−ACNH−2−Py]、[1820:3−CN−4−ACNH−2−Py]、[1821:5−CN−4−ACNH−2−Py]、[1822:6−CN−4−ACNH−2−Py]、[1823:3−OMe−4−ACNH−2−Py]、[1824:5−OMe−4−ACNH−2−Py]、[1825:6−OMe−4−ACNH−2−Py]、[1826:5−ACNH−2−Py]、[1827:3−Cl−5−ACNH−2−Py]、[1828:4−Cl−5−ACNH−2−Py]、[1829:6−Cl−5−ACNH−2−Py]、[1830:3−Me−5−ACNH−2−Py]、[1831:4−Me−5−ACNH−2−Py]、[1832:6−Me−5−ACNH−2−Py]、[1833:3−CF3−5−ACNH−2−Py]、[1834:4−CF3−5−ACNH−2−Py]、[1835:6−CF3−5−ACNH−2−Py]、[1836:3−CN−5−ACNH−2−Py]、[1837:4−CN−5−ACNH−2−Py]、[1838:6−CN−5−ACNH−2−Py]、[1839:3−OMe−5−ACNH−2−Py]、[1840:4−OMe−5−ACNH−2−Py]、[1841:6−OMe−5−ACNH−2−Py]、[1842:6−ACNH−2−Py]、[1843:3−Cl−6−ACNH−2−Py]、[1844:4−Cl−6−ACNH−2−Py]、[1845:5−Cl−6−ACNH−2−Py]、[1846:3−Me−6−ACNH−2−Py]、[1847:4−Me−6−ACNH−2−Py]、[1848:5−Me−6−ACNH−2−Py]、[1849:3−CF3−6−ACNH−2−Py]、[1850:4−CF3−6−ACNH−2−Py]、[1851:5−CF3−6−ACNH−2−Py]、[1852:3−CN−6−ACNH−2−Py]、[1853:4−CN−6−ACNH−2−Py]、[1854:5−CN−6−ACNH−2−Py]、[1855:3−OMe−6−ACNH−2−Py]、[1856:4−OMe−6−ACNH−2−Py]、[1857:5−OMe−6−ACNH−2−Py]、[1858:3−(N−AC−N−Me−N)−2−Py]、[1859:4−Cl−3−(N−AC−N−Me−N)−2−Py]、[1860:5−Cl−3−(N−AC−N−Me−N)−2−Py]、[1861:6−Cl−3−(N−AC−N−Me−N)−2−Py]、[1862:4−Me−3−(N−AC−N−Me−N)−2−Py]、[1863:5−Me−3−(N−AC−N−Me−N)−2−Py]、[1864:6−Me−3−(N−AC−N−Me−N)−2−Py]、[1865:4−CF3−3−(N−AC−N−Me−N)−2−Py]、[1866:5−CF3−3−(N−AC−N−Me−N)−2−Py]、[1867:6−CF3−3−(N−AC−N−Me−N)−2−Py]、[1868:4−CN−3−(N−AC−N−Me−N)−2−Py]、[1869:5−CN−3−(N−AC−N−Me−N)−2−Py]、[1870:6−CN−3−(N−AC−N−Me−N)−2−Py]、[1871:4−OMe−3−(N−AC−N−Me−N)−2−Py]、[1872:5−OMe−3−(N−AC−N−Me−N)−2−Py]、[1873:6−OMe−3−(N−AC−N−Me−N)−2−Py]、[1874:4−(N−AC−N−Me−N)−2−Py]、[1875:3−Cl−4−(N−AC−N−Me−N)−2−Py]、[1876:5−Cl−4−(N−AC−N−Me−N)−2−Py]、[1877:6−Cl−4−(N−AC−N−Me−N)−2−Py]、[1878:3−Me−4−(N−AC−N−Me−N)−2−Py]、[1879:5−Me−4−(N−AC−N−Me−N)−2−Py]、[1880:6−Me−4−(N−AC−N−Me−N)−2−Py]、[1881:3−CF3−4−(N−AC−N−Me−N)−2−Py]、[1882:5−CF3−4−(N−AC−N−Me−N)−2−Py]、[1883:6−CF3−4−(N−AC−N−Me−N)−2−Py]、[1884:3−CN−4−(N−AC−N−Me−N)−2−Py]、[1885:5−CN−4−(N−AC−N−Me−N)−2−Py]、[1886:6−CN−4−(N−AC−N−Me−N)−2−Py]、[1887:3−OMe−4−(N−AC−N−Me−N)−2−Py]、[1888:5−OMe−4−(N−AC−N−Me−N)−2−Py]、[1889:6−OMe−4−(N−AC−N−Me−N)−2−Py]、[1890:5−(N−AC−N−Me−N)−2−Py]、[1891:3−Cl−5−(N−AC−N−Me−N)−2−Py]、[1892:4−Cl−5−(N−AC−N−Me−N)−2−Py]、[1893:6−Cl−5−(N−AC−N−Me−N)−2−Py]、[1894:3−Me−5−(N−AC−N−Me−N)−2−Py]、[1895:4−Me−5−(N−AC−N−Me−N)−2−Py]、[1896:6−Me−5−(N−AC−N−Me−N)−2−Py]、[1897:3−CF3−5−(N−AC−N−Me−N)−2−Py]、[1898:4−CF3−5−(N−AC−N−Me−N)−2−Py]、[1899:6−CF3−5−(N−AC−N−Me−N)−2−Py]、[1900:3−CN−5−(N−AC−N−Me−N)−2−Py]、 [1801: 4-CF3-3-ACNH-2-Py], [1802: 5-CF3-3-ACNH-2-Py], [1803: 6-CF3-3-ACNH-2-Py], [1804 : 4-CN-3-ACNH-2-Py], [1805: 5-CN-3-ACNH-2-Py], [1806: 6-CN-3-ACNH-2-Py], [1807: 4 -OMe-3-ACNH-2-Py], [1808: 5-OMe-3-ACNH-2-Py], [1809: 6-OMe-3-ACNH-2-Py], [1810: 4-ACNH -2-Py], [1811: 3-Cl-4-ACNH-2-Py], [1812: 5-Cl-4-ACNH-2-Py], [1813: 6-Cl-4-ACNH-2 -Py], [1814: 3-Me-4-ACNH-2- y], [1815: 5-Me-4-ACNH-2-Py], [1816: 6-Me-4-ACNH-2-Py], [1817: 3-CF3-4-ACNH-2-Py] [1818: 5-CF3-4-ACNH-2-Py], [1819: 6-CF3-4-ACNH-2-Py], [1820: 3-CN-4-ACNH-2-Py], [ 1821: 5-CN-4-ACNH-2-Py], [1822: 6-CN-4-ACNH-2-Py], [1823: 3-OMe-4-ACNH-2-Py], [1824: 5-OMe-4-ACNH-2-Py], [1825: 6-OMe-4-ACNH-2-Py], [1826: 5-ACNH-2-Py], [1827: 3-Cl-5 ACNH-2-Py], [1828: 4-Cl-5-ACN -2-Py], [1829: 6-Cl-5-ACNH-2-Py], [1830: 3-Me-5-ACNH-2-Py], [1831: 4-Me-5-ACNH-2 -Py], [1832: 6-Me-5-ACNH-2-Py], [1833: 3-CF3-5-ACNH-2-Py], [1834: 4-CF3-5-ACNH-2-Py] ], [1835: 6-CF3-5-ACNH-2-Py], [1836: 3-CN-5-ACNH-2-Py], [1837: 4-CN-5-ACNH-2-Py], [1838: 6-CN-5-ACNH-2-Py], [1839: 3-OMe-5-ACNH-2-Py], [1840: 4-OMe-5-ACNH-2-Py], [1841 : 6-OMe-5-ACNH-2-Py], [1842: 6- ACNH-2-Py], [1843: 3-Cl-6-ACNH-2-Py], [1844: 4-Cl-6-ACNH-2-Py], [1845: 5-Cl-6-ACNH- 2-Py], [1846: 3-Me-6-ACNH-2-Py], [1847: 4-Me-6-ACNH-2-Py], [1848: 5-Me-6-ACNH-2- Py], [1849: 3-CF3-6-ACNH-2-Py], [1850: 4-CF3-6-ACNH-2-Py], [1851: 5-CF3-6-ACNH-2-Py] [1852: 3-CN-6-ACNH-2-Py], [1853: 4-CN-6-ACNH-2-Py], [1854: 5-CN-6-ACNH-2-Py], [ 1855: 3-OMe-6-ACNH-2-Py], [1856: -OMe-6-ACNH-2-Py], [1857: 5-OMe-6-ACNH-2-Py], [1858: 3- (N-AC-N-Me-N) -2-Py], [1859: 4-Cl-3- (N-AC-N-Me-N) -2-Py], [1860: 5-Cl-3- (N-AC-N-Me-N) -2-Py ], [1861: 6-Cl-3- (N-AC-N-Me-N) -2-Py], [1862: 4-Me-3- (N-AC-N-Me-N) -2 -Py], [1863: 5-Me-3- (N-AC-N-Me-N) -2-Py], [1864: 6-Me-3- (N-AC-N-Me-N) -2-Py], [1865: 4-CF3-3 (N-AC-N-Me-N) -2-Py], [1866: 5-CF3-3 (N-AC-N-Me-) N) -2 Py], [1867: 6-CF3-3 (N-AC-N-Me-N) -2-Py], [1868: 4-CN-3- (N-AC-N-Me-N)- 2-Py], [1869: 5-CN-3- (N-AC-N-Me-N) -2-Py], [1870: 6-CN-3- (N-AC-N-Me-N) ) -2-Py], [1871: 4-OMe-3- (N-AC-N-Me-N) -2-Py], [1872: 5-OMe-3- (N-AC-N-Me). -N) -2-Py], [1873: 6-OMe-3- (N-AC-N-Me-N) -2-Py], [1874: 4- (N-AC-N-Me-N). ) -2-Py], [1875: 3-Cl-4- (N-AC-N-Me-N) -2-Py], [1876: 5-Cl-4- (N-AC-N-Me). -N) -2-Py], [1877: 6-Cl-4- (N-AC-N-Me-N) -2-Py], [1878: 3-Me-4- (N-AC-N-Me-N) -2-Py ], [1879: 5-Me-4- (N-AC-N-Me-N) -2-Py], [1880: 6-Me-4- (N-AC-N-Me-N) -2. -Py], [1881: 3-CF3-4- (N-AC-N-Me-N) -2-Py], [1882: 5-CF3-4- (N-AC-N-Me-N) -2-Py], [1883: 6-CF3-4- (N-AC-N-Me-N) -2-Py], [1884: 3-CN-4- (N-AC-N-Me- N) -2-Py], [1885: 5-CN-4- (N-AC-N-Me-N) -2-Py], [1886: 6-CN-4- (N-AC-N- Me-N) -2-Py], 1887: 3-OMe-4- (N-AC-N-Me-N) -2-Py], [1888: 5-OMe-4- (N-AC-N-Me-N) -2-Py] [1889: 6-OMe-4- (N-AC-N-Me-N) -2-Py], [1890: 5- (N-AC-N-Me-N) -2-Py], [ 1891: 3-Cl-5- (N-AC-N-Me-N) -2-Py], [1892: 4-Cl-5- (N-AC-N-Me-N) -2-Py] [1893: 6-Cl-5- (N-AC-N-Me-N) -2-Py], [1894: 3-Me-5- (N-AC-N-Me-N) -2- Py], [1895: 4-Me-5- (N-AC-N-Me-N) -2-Py], [1896: 6-Me-5- (N-AC-N-Me-N)- 2-Py], [1897 3-CF3-5- (N-AC-N-Me-N) -2-Py], [1898: 4-CF3-5- (N-AC-N-Me-N) -2-Py], [ 1899: 6-CF3-5- (N-AC-N-Me-N) -2-Py], [1900: 3-CN-5- (N-AC-N-Me-N) -2-Py] ,
[1901:4−CN−5−(N−AC−N−Me−N)−2−Py]、[1902:6−CN−5−(N−AC−N−Me−N)−2−Py]、[1903:3−OMe−5−(N−AC−N−Me−N)−2−Py]、[1904:4−OMe−5−(N−AC−N−Me−N)−2−Py]、[1905:6−OMe−5−(N−AC−N−Me−N)−2−Py]、[1906:6−(N−AC−N−Me−N)−2−Py]、[1907:3−Cl−6−(N−AC−N−Me−N)−2−Py]、[1908:4−Cl−6−(N−AC−N−Me−N)−2−Py]、[1909:5−Cl−6−(N−AC−N−Me−N)−2−Py]、[1910:3−Me−6−(N−AC−N−Me−N)−2−Py]、[1911:4−Me−6−(N−AC−N−Me−N)−2−Py]、[1912:5−Me−6−(N−AC−N−Me−N)−2−Py]、[1913:3−CF3−6−(N−AC−N−Me−N)−2−Py]、[1914:4−CF3−6−(N−AC−N−Me−N)−2−Py]、[1915:5−CF3−6−(N−AC−N−Me−N)−2−Py]、[1916:3−CN−6−(N−AC−N−Me−N)−2−Py]、[1917:4−CN−6−(N−AC−N−Me−N)−2−Py]、[1918:5−CN−6−(N−AC−N−Me−N)−2−Py]、[1919:3−OMe−6−(N−AC−N−Me−N)−2−Py]、[1920:4−OMe−6−(N−AC−N−Me−N)−2−Py]、[1921:5−OMe−6−(N−AC−N−Me−N)−2−Py]、[1922:3−AC−2−Py]、[1923:4−Cl−3−AC−2−Py]、[1924:5−Cl−3−AC−2−Py]、[1925:6−Cl−3−AC−2−Py]、[1926:4−Me−3−AC−2−Py]、[1927:5−Me−3−AC−2−Py]、[1928:6−Me−3−AC−2−Py]、[1929:4−CF3−3−AC−2−Py]、[1930:5−CF3−3−AC−2−Py]、[1931:6−CF3−3−AC−2−Py]、[1932:4−CN−3−AC−2−Py]、[1933:5−CN−3−AC−2−Py]、[1934:6−CN−3−AC−2−Py]、[1935:4−OMe−3−AC−2−Py]、[1936:5−OMe−3−AC−2−Py]、[1937:6−OMe−3−AC−2−Py]、[1938:4−AC−2−Py]、[1939:3−Cl−4−AC−2−Py]、[1940:5−Cl−4−AC−2−Py]、[1941:6−Cl−4−AC−2−Py]、[1942:3−Me−4−AC−2−Py]、[1943:5−Me−4−AC−2−Py]、[1944:6−Me−4−AC−2−Py]、[1945:3−CF3−4−AC−2−Py]、[1946:5−CF3−4−AC−2−Py]、[1947:6−CF3−4−AC−2−Py]、[1948:3−CN−4−AC−2−Py]、[1949:5−CN−4−AC−2−Py]、[1950:6−CN−4−AC−2−Py]、[1951:3−OMe−4−AC−2−Py]、[1952:5−OMe−4−AC−2−Py]、[1953:6−OMe−4−AC−2−Py]、[1954:5−AC−2−Py]、[1955:3−Cl−5−AC−2−Py]、[1956:4−Cl−5−AC−2−Py]、[1957:6−Cl−5−AC−2−Py]、[1958:3−Me−5−AC−2−Py]、[1959:4−Me−5−AC−2−Py]、[1960:6−Me−5−AC−2−Py]、[1961:3−CF3−5−AC−2−Py]、[1962:4−CF3−5−AC−2−Py]、[1963:6−CF3−5−AC−2−Py]、[1964:3−CN−5−AC−2−Py]、[1965:4−CN−5−AC−2−Py]、[1966:6−CN−5−AC−2−Py]、[1967:3−OMe−5−AC−2−Py]、[1968:4−OMe−5−AC−2−Py]、[1969:6−OMe−5−AC−2−Py]、[1970:6−AC−2−Py]、[1971:3−Cl−6−AC−2−Py]、[1972:4−Cl−6−AC−2−Py]、[1973:5−Cl−6−AC−2−Py]、[1974:3−Me−6−AC−2−Py]、[1975:4−Me−6−AC−2−Py]、[1976:5−Me−6−AC−2−Py]、[1977:3−CF3−6−AC−2−Py]、[1978:4−CF3−6−AC−2−Py]、[1979:5−CF3−6−AC−2−Py]、[1980:3−CN−6−AC−2−Py]、[1981:4−CN−6−AC−2−Py]、[1982:5−CN−6−AC−2−Py]、[1983:3−OMe−6−AC−2−Py]、[1984:4−OMe−6−AC−2−Py]、[1985:5−OMe−6−AC−2−Py]、[1986:3−Py]、[1987:2−F−3−Py]、[1988:4−Cl−2−F−3−Py]、[1989:5−Cl−2−F−3−Py]、[1990:6−Cl−2−F−3−Py]、[1991:4−Me−2−F−3−Py]、[1992:5−Me−2−F−3−Py]、[1993:6−Me−2−F−3−Py]、[1994:4−CF3−2−F−3−Py]、[1995:5−CF3−2−F−3−Py]、[1996:6−CF3−2−F−3−Py]、[1997:4−CN−2−F−3−Py]、[1998:5−CN−2−F−3−Py]、[1999:6−CN−2−F−3−Py]、[2000:4−OMe−2−F−3−Py]、 [1901: 4-CN-5- (N-AC-N-Me-N) -2-Py], [1902: 6-CN-5- (N-AC-N-Me-N) -2-Py ], [1903: 3-OMe-5- (N-AC-N-Me-N) -2-Py], [1904: 4-OMe-5- (N-AC-N-Me-N) -2 -Py], [1905: 6-OMe-5- (N-AC-N-Me-N) -2-Py], [1906: 6- (N-AC-N-Me-N) -2-Py ], [1907: 3-Cl-6- (N-AC-N-Me-N) -2-Py], [1908: 4-Cl-6- (N-AC-N-Me-N) -2. -Py], [1909: 5-Cl-6- (N-AC-N-Me-N) -2-Py], [1910: 3-Me-6- (N-AC-N-Me-N) -2-Py], [1911 4-Me-6- (N-AC-N-Me-N) -2-Py], [1912: 5-Me-6- (N-AC-N-Me-N) -2-Py], [ 1913: 3-CF3-6- (N-AC-N-Me-N) -2-Py], [1914: 4-CF3-6- (N-AC-N-Me-N) -2-Py] [1915: 5-CF3-6- (N-AC-N-Me-N) -2-Py], [1916: 3-CN-6- (N-AC-N-Me-N) -2- Py], [1917: 4-CN-6- (N-AC-N-Me-N) -2-Py], [1918: 5-CN-6- (N-AC-N-Me-N)- 2-Py], [1919: 3-OMe-6- (N-AC-N-Me-N) -2-Py], [1920: 4-OMe-6- (N-AC-N-Me-N). ) -2-Py], [19 1: 5-OMe-6- (N-AC-N-Me-N) -2-Py], [1922: 3-AC-2-Py], [1923: 4-Cl-3-AC-2- Py], [1924: 5-Cl-3-AC-2-Py], [1925: 6-Cl-3-AC-2-Py], [1926: 4-Me-3-AC-2-Py] [1927: 5-Me-3-AC-2-Py], [1928: 6-Me-3-AC-2-Py], [1929: 4-CF3-3-AC-2-Py], [ 1930: 5-CF3-3-3-AC-2-Py], [1931: 6-CF3-3-3-AC-2-Py], [1932: 4-CN-3-AC-2-Py], [1933: 5-CN-3-AC-2-Py], [1934: 6-CN-3-AC-2-Py], [1935: 4-OMe-3-AC-2- Py], [1936: 5-OMe-3-AC-2-Py], [1937: 6-OMe-3-AC-2-Py], [1937: 4-AC-2-Py], [1939: 3-Cl-4-AC-2-Py], [1940: 5-Cl-4-AC-2-Py], [1941: 6-Cl-4-AC-2-Py], [1942: 3- Me-4-AC-2-Py], [1943: 5-Me-4-AC-2-Py], [1944: 6-Me-4-AC-2-Py], [1945: 3-CF3- 4-AC-2-Py], [1946: 5-CF3-4-AC-2-Py], [1947: 6-CF3-4-AC-2-Py], [1948: 3-CN-4- AC-2-Py], [1949: 5-CN-4-AC-2-Py], [1950: 6-CN-4-AC-2-Py] [1951: 3-OMe-4-AC-2-Py], [1952: 5-OMe-4-AC-2-Py], [1953: 6-OMe-4-AC-2-Py], [1954 : 5-AC-2-Py], [1955: 3-Cl-5-AC-2-Py], [1956: 4-Cl-5-AC-2-Py], [1957: 6-Cl-5. -AC-2-Py], [1958: 3-Me-5-AC-2-Py], [1959: 4-Me-5-AC-2-Py], [1960: 6-Me-5-AC. -2-Py], [1961: 3-CF3-5-AC-2-Py], [1962: 4-CF3-5-AC-2-Py], [1963: 6-CF3-5-AC-2 -Py], [1964: 3-CN-5-AC-2-Py], [1965: 4-CN-5-AC-2-Py], [ 966: 6-CN-5-AC-2-Py], [1967: 3-OMe-5-AC-2-Py], [1968: 4-OMe-5-AC-2-Py], [1969: 6-OMe-5-AC-2-Py], [1970: 6-AC-2-Py], [1971: 3-Cl-6-AC-2-Py], [1972: 4-Cl-6 AC-2-Py], [1973: 5-Cl-6-AC-2-Py], [1974: 3-Me-6-AC-2-Py], [1975: 4-Me-6-AC- 2-Py], [1976: 5-Me-6-AC-2-Py], [1977: 3-CF3-6-AC-2-Py], [1978: 4-CF3-6-AC-2- Py], [1979: 5-CF3-6-AC-2-Py], [1980: 3-CN-6-AC-2-Py], [198 1: 4-CN-6-AC-2-Py], [1982: 5-CN-6-AC-2-Py], [1983: 3-OMe-6-AC-2-Py], [1984: 4-OMe-6-AC-2-Py], [1985: 5-OMe-6-AC-2-Py], [1986: 3-Py], [1987: 2-F-3-Py], [ 1988: 4-Cl-2-F-3-Py], [1989: 5-Cl-2-F-3-Py], [1990: 6-Cl-2-F-3-Py], [1991: 4-Me-2-F-3-Py], [1992: 5-Me-2-F-3-Py], [1993: 6-Me-2-F-3-Py], [1994: 4- CF3-2-F-3-Py], [1995: 5-CF3-2-F-3-Py], [1996: 6-CF3-2-F-3-Py], [199 : 4-CN-2-F-3-Py], [1998: 5-CN-2-F-3-Py], [1999: 6-CN-2-F-3-Py], [2000: 4 -OMe-2-F-3-Py],
[2001:5−OMe−2−F−3−Py]、[2002:6−OMe−2−F−3−Py]、[2003:4−F−3−Py]、[2004:2−Cl−4−F−3−Py]、[2005:5−Cl−4−F−3−Py]、[2006:6−Cl−4−F−3−Py]、[2007:2−Me−4−F−3−Py]、[2008:5−Me−4−F−3−Py]、[2009:6−Me−4−F−3−Py]、[2010:2−CF3−4−F−3−Py]、[2011:5−CF3−4−F−3−Py]、[2012:6−CF3−4−F−3−Py]、[2013:2−CN−4−F−3−Py]、[2014:5−CN−4−F−3−Py]、[2015:6−CN−4−F−3−Py]、[2016:2−OMe−4−F−3−Py]、[2017:5−OMe−4−F−3−Py]、[2018:6−OMe−4−F−3−Py]、[2019:5−F−3−Py]、[2020:2−Cl−5−F−3−Py]、[2021:4−Cl−5−F−3−Py]、[2022:6−Cl−5−F−3−Py]、[2023:2−Me−5−F−3−Py]、[2024:4−Me−5−F−3−Py]、[2025:6−Me−5−F−3−Py]、[2026:2−CF3−5−F−3−Py]、[2027:4−CF3−5−F−3−Py]、[2028:6−CF3−5−F−3−Py]、[2029:2−CN−5−F−3−Py]、[2030:4−CN−5−F−3−Py]、[2031:6−CN−5−F−3−Py]、[2032:2−OMe−5−F−3−Py]、[2033:4−OMe−5−F−3−Py]、[2034:6−OMe−5−F−3−Py]、[2035:6−F−3−Py]、[2036:2−Cl−6−F−3−Py]、[2037:4−Cl−6−F−3−Py]、[2038:5−Cl−6−F−3−Py]、[2039:2−Me−6−F−3−Py]、[2040:4−Me−6−F−3−Py]、[2041:5−Me−6−F−3−Py]、[2042:2−CF3−6−F−3−Py]、[2043:4−CF3−6−F−3−Py]、[2044:5−CF3−6−F−3−Py]、[2045:2−CN−6−F−3−Py]、[2046:4−CN−6−F−3−Py]、[2047:5−CN−6−F−3−Py]、[2048:2−OMe−6−F−3−Py]、[2049:4−OMe−6−F−3−Py]、[2050:5−OMe−6−F−3−Py]、[2051:2−Cl−3−Py]、[2052:4−Cl−2−Cl−3−Py]、[2053:5−Cl−2−Cl−3−Py]、[2054:6−Cl−2−Cl−3−Py]、[2055:4−Me−2−Cl−3−Py]、[2056:5−Me−2−Cl−3−Py]、[2057:6−Me−2−Cl−3−Py]、[2058:4−CF3−2−Cl−3−Py]、[2059:5−CF3−2−Cl−3−Py]、[2060:6−CF3−2−Cl−3−Py]、[2061:4−CN−2−Cl−3−Py]、[2062:5−CN−2−Cl−3−Py]、[2063:6−CN−2−Cl−3−Py]、[2064:4−OMe−2−Cl−3−Py]、[2065:5−OMe−2−Cl−3−Py]、[2066:6−OMe−2−Cl−3−Py]、[2067:4−Cl−3−Py]、[2068:2−Cl−4−Cl−3−Py]、[2069:5−Cl−4−Cl−3−Py]、[2070:6−Cl−4−Cl−3−Py]、[2071:2−Me−4−Cl−3−Py]、[2072:5−Me−4−Cl−3−Py]、[2073:6−Me−4−Cl−3−Py]、[2074:2−CF3−4−Cl−3−Py]、[2075:5−CF3−4−Cl−3−Py]、[2076:6−CF3−4−Cl−3−Py]、[2077:2−CN−4−Cl−3−Py]、[2078:5−CN−4−Cl−3−Py]、[2079:6−CN−4−Cl−3−Py]、[2080:2−OMe−4−Cl−3−Py]、[2081:5−OMe−4−Cl−3−Py]、[2082:6−OMe−4−Cl−3−Py]、[2083:5−Cl−3−Py]、[2084:4−Cl−5−Cl−3−Py]、[2085:5−Cl−5−Cl−3−Py]、[2086:6−Cl−5−Cl−3−Py]、[2087:4−Me−5−Cl−3−Py]、[2088:5−Me−5−Cl−3−Py]、[2089:6−Me−5−Cl−3−Py]、[2090:4−CF3−5−Cl−3−Py]、[2091:5−CF3−5−Cl−3−Py]、[2092:6−CF3−5−Cl−3−Py]、[2093:4−CN−5−Cl−3−Py]、[2094:3−CN−5−Cl−3−Py]、[2095:6−CN−5−Cl−3−Py]、[2096:4−OMe−5−Cl−3−Py]、[2097:5−OMe−5−Cl−3−Py]、[2098:6−OMe−5−Cl−3−Py]、[2099:6−Cl−3−Py]、[2100:2−Cl−6−Cl−3−Py]、 [2001: 5-OMe-2-F-3-Py], [2002: 6-OMe-2-F-3-Py], [2003: 4-F-3-Py], [2004: 2-Cl -4-F-3-Py], [2005: 5-Cl-4-F-3-Py], [2006: 6-Cl-4-F-3-Py], [2007: 2-Me-4 -F-3-Py], [2008: 5-Me-4-F-3-Py], [2009: 6-Me-4-F-3-Py], [2010: 2-CF3-4-F -3-Py], [2011: 5-CF3-4-F-3-Py], [2012: 6-CF3-4-F-3-Py], [2013: 2-CN-4-F-3] -Py], [2014: 5-CN-4-F-3-Py], [2015: 6-CN-4-F-3-Py], [2016: 2-OMe-4-F-3- y], [2017: 5-OMe-4-F-3-Py], [2018: 6-OMe-4-F-3-Py], [2019: 5-F-3-Py], [2020: 2-Cl-5-F-3-Py], [2021: 4-Cl-5-F-3-Py], [2022: 6-Cl-5-F-3-Py], [2023: 2- Me-5-F-3-Py], [2024: 4-Me-5-F-3-Py], [2025: 6-Me-5-F-3-Py], [2026: 2-CF3- 5-F-3-Py], [2027: 4-CF3-5-F-3-Py], [2028: 6-CF3-5-F-3-Py], [2029: 2-CN-5 F-3-Py], [2030: 4-CN-5-F-3-Py], [2031: 6-CN-5-F-3-Py], [2032: 2-OMe-5-5 -3-Py], [2033: 4-OMe-5-F-3-Py], [2034: 6-OMe-5-F-3-Py], [2035: 6-F-3-Py], [2036: 2-Cl-6-F-3-Py], [2037: 4-Cl-6-F-3-Py], [2038: 5-Cl-6-F-3-Py], [2039 : 2-Me-6-F-3-Py], [2040: 4-Me-6-F-3-Py], [2041: 5-Me-6-F-3-Py], [2042: 2 -CF3-6-F-3-Py], [2043: 4-CF3-6-F-3-Py], [2044: 5-CF3-6-F-3-Py], [2045: 2-CN -6-F-3-Py], [2046: 4-CN-6-F-3-Py], [2047: 5-CN-6-F-3-Py], [2048: 2-OMe. -6-F-3-Py], [2049: 4-OMe-6-F-3-Py], [2050: 5-OMe-6-F-3-Py], [2051: 2-Cl-3. -Py], [2052: 4-Cl-2-Cl-3-Py], [2053: 5-Cl-2-Cl-3-Py], [2054: 6-Cl-2-Cl-3-Py ], [2055: 4-Me-2-Cl-3-Py], [2056: 5-Me-2-Cl-3-Py], [2057: 6-Me-2-Cl-3-Py], [2058: 4-CF3-2-Cl-3-Py], [2059: 5-CF3-2-Cl-3-Py], [2060: 6-CF3-2-Cl-3-Py], [2061] : 4-CN-2-Cl-3-Py], [2062: 5-CN-2-Cl-3-Py], [2063: 6-CN-2-Cl- -Py], [2064: 4-OMe-2-Cl-3-Py], [2065: 5-OMe-2-Cl-3-Py], [2066: 6-OMe-2-Cl-3-Py ], [2067: 4-Cl-3-Py], [2068: 2-Cl-4-Cl-3-Py], [2069: 5-Cl-4-Cl-3-Py], [2070: 6] -Cl-4-Cl-3-Py], [2071: 2-Me-4-Cl-3-Py], [2072: 5-Me-4-Cl-3-Py], [2073: 6-Me -4-Cl-3-Py], [2074: 2-CF3-4-Cl-3-Py], [2075: 5-CF3-4-Cl-3-Py], [2076: 6-CF3-4 -Cl-3-Py], [2077: 2-CN-4-Cl-3-Py], [2078: 5-CN-4-Cl-3- y], [2079: 6-CN-4-Cl-3-Py], [2080: 2-OMe-4-Cl-3-Py], [2081: 5-OMe-4-Cl-3-Py] [2082: 6-OMe-4-Cl-3-Py], [2083: 5-Cl-3-Py], [2084: 4-Cl-5-Cl-3-Py], [2085: 5- Cl-5-Cl-3-Py], [2086: 6-Cl-5-Cl-3-Py], [2087: 4-Me-5-Cl-3-Py], [2088: 5-Me- 5-Cl-3-Py], [2089: 6-Me-5-Cl-3-Py], [2090: 4-CF3-5-Cl-3-Py], [2091: 5-CF3-5 Cl-3-Py], [2092: 6-CF3-5-Cl-3-Py], [2093: 4-CN-5-Cl-3-Py] [2094: 3-CN-5-Cl-3-Py], [2095: 6-CN-5-Cl-3-Py], [2096: 4-OMe-5-Cl-3-Py], [ 2097: 5-OMe-5-Cl-3-Py], [2098: 6-OMe-5-Cl-3-Py], [2099: 6-Cl-3-Py], [2100: 2-Cl- 6-Cl-3-Py],
[2101:4−Cl−6−Cl−3−Py]、[2102:5−Cl−6−Cl−3−Py]、[2103:2−Me−6−Cl−3−Py]、[2104:4−Me−6−Cl−3−Py]、[2105:5−Me−6−Cl−3−Py]、[2106:2−CF3−6−Cl−3−Py]、[2107:4−CF3−6−Cl−3−Py]、[2108:5−CF3−6−Cl−3−Py]、[2109:2−CN−6−Cl−3−Py]、[2110:4−CN−6−Cl−3−Py]、[2111:5−CN−6−Cl−3−Py]、[2112:2−OMe−6−Cl−3−Py]、[2113:4−OMe−6−Cl−3−Py]、[2114:5−OMe−6−Cl−3−Py]、[2115:2−Br−3−Py]、[2116:4−Cl−2−Br−3−Py]、[2117:5−Cl−2−Br−3−Py]、[2118:6−Cl−2−Br−3−Py]、[2119:4−Me−2−Br−3−Py]、[2120:5−Me−2−Br−3−Py]、[2121:6−Me−2−Br−3−Py]、[2122:4−CF3−2−Br−3−Py]、[2123:5−CF3−2−Br−3−Py]、[2124:6−CF3−2−Br−3−Py]、[2125:4−CN−2−Br−3−Py]、[2126:5−CN−2−Br−3−Py]、[2127:6−CN−2−Br−3−Py]、[2128:4−OMe−2−Br−3−Py]、[2129:5−OMe−2−Br−3−Py]、[2130:6−OMe−2−Br−3−Py]、[2131:4−Br−3−Py]、[2132:2−Cl−4−Br−3−Py]、[2133:5−Cl−4−Br−3−Py]、[2134:6−Cl−4−Br−3−Py]、[2135:2−Me−4−Br−3−Py]、[2136:5−Me−4−Br−3−Py]、[2137:6−Me−4−Br−3−Py]、[2138:2−CF3−4−Br−3−Py]、[2139:5−CF3−4−Br−3−Py]、[2140:6−CF3−4−Br−3−Py]、[2141:2−CN−4−Br−3−Py]、[2142:5−CN−4−Br−3−Py]、[2143:6−CN−4−Br−3−Py]、[2144:2−OMe−4−Br−3−Py]、[2145:5−OMe−4−Br−3−Py]、[2146:6−OMe−4−Br−3−Py]、[2147:5−Br−3−Py]、[2148:2−Cl−5−Br−3−Py]、[2149:4−Cl−5−Br−3−Py]、[2150:6−Cl−5−Br−3−Py]、[2151:2−Me−5−Br−3−Py]、[2152:4−Me−5−Br−3−Py]、[2153:6−Me−5−Br−3−Py]、[2154:2−CF3−5−Br−3−Py]、[2155:4−CF3−5−Br−3−Py]、[2156:6−CF3−5−Br−3−Py]、[2157:2−CN−5−Br−3−Py]、[2158:4−CN−5−Br−3−Py]、[2159:6−CN−5−Br−3−Py]、[2160:2−OMe−5−Br−3−Py]、[2161:4−OMe−5−Br−3−Py]、[2162:6−OMe−5−Br−3−Py]、[2163:6−Br−3−Py]、[2164:2−Cl−6−Br−3−Py]、[2165:4−Cl−6−Br−3−Py]、[2166:5−Cl−6−Br−3−Py]、[2167:2−Me−6−Br−3−Py]、[2168:4−Me−6−Br−3−Py]、[2169:5−Me−6−Br−3−Py]、[2170:2−CF3−6−Br−3−Py]、[2171:4−CF3−6−Br−3−Py]、[2172:5−CF3−6−Br−3−Py]、[2173:2−CN−6−Br−3−Py]、[2174:4−CN−6−Br−3−Py]、[2175:5−CN−6−Br−3−Py]、[2176:2−OMe−6−Br−3−Py]、[2177:4−OMe−6−Br−3−Py]、[2178:5−OMe−6−Br−3−Py]、[2179:2−I−3−Py]、[2180:4−Cl−2−I−3−Py]、[2181:5−Cl−2−I−3−Py]、[2182:6−Cl−2−I−3−Py]、[2183:4−Me−2−I−3−Py]、[2184:5−Me−2−I−3−Py]、[2185:6−Me−2−I−3−Py]、[2186:4−CF3−2−I−3−Py]、[2187:5−CF3−2−I−3−Py]、[2188:6−CF3−2−I−3−Py]、[2189:4−CN−2−I−3−Py]、[2190:5−CN−2−I−3−Py]、[2191:6−CN−2−I−3−Py]、[2192:4−OMe−2−I−3−Py]、[2193:5−OMe−2−I−3−Py]、[2194:6−OMe−2−I−3−Py]、[2195:4−I−3−Py]、[2196:2−Cl−4−I−3−Py]、[2197:5−Cl−4−I−3−Py]、[2198:6−Cl−4−I−3−Py]、[2199:2−Me−4−I−3−Py]、[2200:5−Me−4−I−3−Py]、 [2101: 4-Cl-6-Cl-3-Py], [2102: 5-Cl-6-Cl-3-Py], [2103: 2-Me-6-Cl-3-Py], [2104 : 4-Me-6-Cl-3-Py], [2105: 5-Me-6-Cl-3-Py], [2106: 2-CF3-6-Cl-3-Py], [2107: 4 -CF3-6-Cl-3-Py], [2108: 5-CF3-6-Cl-3-Py], [2109: 2-CN-6-Cl-3-Py], [2110: 4-CN -6-Cl-3-Py], [2111: 5-CN-6-Cl-3-Py], [2112: 2-OMe-6-Cl-3-Py], [2113: 4-OMe-6 -Cl-3-Py], [2114: 5-OMe-6-Cl-3-Py], [2115: 2-Br-3-Py], [2 16: 4-Cl-2-Br-3-Py], [2117: 5-Cl-2-Br-3-Py], [2118: 6-Cl-2-Br-3-Py], [2119: 4-Me-2-Br-3-Py], [2120: 5-Me-2-Br-3-Py], [2121: 6-Me-2-Br-3-Py], [2122: 4- CF3-2-Br-3-Py], [2123: 5-CF3-2-Br-3-Py], [2124: 6-CF3-2-Br-3-Py], [2125: 4-CN- 2-Br-3-Py], [2126: 5-CN-2-Br-3-Py], [2127: 6-CN-2-Br-3-Py], [2128: 4-OMe-2- Br-3-Py], [2129: 5-OMe-2-Br-3-Py], [2130: 6-OMe-2-Br-3-Py] [2131: 4-Br-3-Py], [2132: 2-Cl-4-Br-3-Py], [2133: 5-Cl-4-Br-3-Py], [2134: 6-Cl -4-Br-3-Py], [2135: 2-Me-4-Br-3-Py], [2136: 5-Me-4-Br-3-Py], [2137: 6-Me-4 -Br-3-Py], [2138: 2-CF3-4-Br-3-Py], [2139: 5-CF3-4-Br-3-Py], [2140: 6-CF3-4-Br -3-Py], [2141: 2-CN-4-Br-3-Py], [2142: 5-CN-4-Br-3-Py], [2143: 6-CN-4-Br-3. -Py], [2144: 2-OMe-4-Br-3-Py], [2145: 5-OMe-4-Br-3-Py], [21 46: 6-OMe-4-Br-3-Py], [2147: 5-Br-3-Py], [2148: 2-Cl-5-Br-3-Py], [2149: 4-Cl- 5-Br-3-Py], [2150: 6-Cl-5-Br-3-Py], [2151: 2-Me-5-Br-3-Py], [2152: 4-Me-5 Br-3-Py], [2153: 6-Me-5-Br-3-Py], [2154: 2-CF3-5-Br-3-Py], [2155: 4-CF3-5-Br- 3-Py], [2156: 6-CF3-5-Br-3-Py], [2157: 2-CN-5-Br-3-Py], [2158: 4-CN-5-Br-3- Py], [2159: 6-CN-5-Br-3-Py], [2160: 2-OMe-5-Br-3-Py], [2161: -OMe-5-Br-3-Py], [2162: 6-OMe-5-Br-3-Py], [2163: 6-Br-3-Py], [2164: 2-Cl-6-Br -3-Py], [2165: 4-Cl-6-Br-3-Py], [2166: 5-Cl-6-Br-3-Py], [2167: 2-Me-6-Br-3 -Py], [2168: 4-Me-6-Br-3-Py], [2169: 5-Me-6-Br-3-Py], [2170: 2-CF3-6-Br-3-Py] ], [2171: 4-CF3-6-Br-3-Py], [2172: 5-CF3-6-Br-3-Py], [2173: 2-CN-6-Br-3-Py], [2174: 4-CN-6-Br-3-Py], [2175: 5-CN-6-Br-3-Py], [2176: 2-O e-6-Br-3-Py], [2177: 4-OMe-6-Br-3-Py], [2178: 5-OMe-6-Br-3-Py], [2179: 2-I- 3-Py], [2180: 4-Cl-2-I-3-Py], [2181: 5-Cl-2-I-3-Py], [2182: 6-Cl-2-I-3- Py], [2183: 4-Me-2-I-3-Py], [2184: 5-Me-2-I-3-Py], [2185: 6-Me-2-I-3-Py] [2186: 4-CF3-2-I-3-Py], [2187: 5-CF3-2-I-3-Py], [2188: 6-CF3-2-I-3-Py], [ 2189: 4-CN-2-I-3-Py], [2190: 5-CN-2-I-3-Py], [2191: 6-CN-2-I-3-Py], [21 92: 4-OMe-2-I-3-Py], [2193: 5-OMe-2-I-3-Py], [2194: 6-OMe-2-I-3-Py], [2195: 4-I-3-Py], [2196: 2-Cl-4-I-3-Py], [2197: 5-Cl-4-I-3-Py], [2198: 6-Cl-4- I-3-Py], [2199: 2-Me-4-I-3-Py], [2200: 5-Me-4-I-3-Py],
[2201:6−Me−4−I−3−Py]、[2202:2−CF3−4−I−3−Py]、[2203:5−CF3−4−I−3−Py]、[2204:6−CF3−4−I−3−Py]、[2205:2−CN−4−I−3−Py]、[2206:5−CN−4−I−3−Py]、[2207:6−CN−4−I−3−Py]、[2208:2−OMe−4−I−3−Py]、[2209:5−OMe−4−I−3−Py]、[2210:6−OMe−4−I−3−Py]、[2211:5−I−3−Py]、[2212:2−Cl−5−I−3−Py]、[2213:4−Cl−5−I−3−Py]、[2214:6−Cl−5−I−3−Py]、[2215:2−Me−5−I−3−Py]、[2216:4−Me−5−I−3−Py]、[2217:6−Me−5−I−3−Py]、[2218:2−CF3−5−I−3−Py]、[2219:4−CF3−5−I−3−Py]、[2220:6−CF3−5−I−3−Py]、[2221:2−CN−5−I−3−Py]、[2222:4−CN−5−I−3−Py]、[2223:6−CN−5−I−3−Py]、[2224:2−OMe−5−I−3−Py]、[2225:4−OMe−5−I−3−Py]、[2226:6−OMe−5−I−3−Py]、[2227:6−I−3−Py]、[2228:2−Cl−6−I−3−Py]、[2229:4−Cl−6−I−3−Py]、[2230:5−Cl−6−I−3−Py]、[2231:2−Me−6−I−3−Py]、[2232:4−Me−6−I−3−Py]、[2233:5−Me−6−I−3−Py]、[2234:2−CF3−6−I−3−Py]、[2235:4−CF3−6−I−3−Py]、[2236:5−CF3−6−I−3−Py]、[2237:2−CN−6−I−3−Py]、[2238:4−CN−6−I−3−Py]、[2239:5−CN−6−I−3−Py]、[2240:2−OMe−6−I−3−Py]、[2241:4−OMe−6−I−3−Py]、[2242:5−OMe−6−I−3−Py]、[2243:2−Me−3−Py]、[2244:4−Cl−2−Me−3−Py]、[2245:5−Cl−2−Me−3−Py]、[2246:6−Cl−2−Me−3−Py]、[2247:4−Me−2−Me−3−Py]、[2248:5−Me−2−Me−3−Py]、[2249:6−Me−2−Me−3−Py]、[2250:4−CF3−2−Me−3−Py]、[2251:5−CF3−2−Me−3−Py]、[2252:6−CF3−2−Me−3−Py]、[2253:4−CN−2−Me−3−Py]、[2254:5−CN−2−Me−3−Py]、[2255:6−CN−2−Me−3−Py]、[2256:4−OMe−2−Me−3−Py]、[2257:5−OMe−2−Me−3−Py]、[2258:6−OMe−2−Me−3−Py]、[2259:4−Me−3−Py]、[2260:2−Cl−4−Me−3−Py]、[2261:5−Cl−4−Me−3−Py]、[2262:6−Cl−4−Me−3−Py]、[2263:2−Me−4−Me−3−Py]、[2264:5−Me−4−Me−3−Py]、[2265:6−Me−4−Me−3−Py]、[2266:2−CF3−4−Me−3−Py]、[2267:5−CF3−4−Me−3−Py]、[2268:6−CF3−4−Me−3−Py]、[2269:2−CN−4−Me−3−Py]、[2270:5−CN−4−Me−3−Py]、[2271:6−CN−4−Me−3−Py]、[2272:2−OMe−4−Me−3−Py]、[2273:5−OMe−4−Me−3−Py]、[2274:6−OMe−4−Me−3−Py]、[2275:5−Me−3−Py]、[2276:2−Cl−5−Me−3−Py]、[2277:4−Cl−5−Me−3−Py]、[2278:6−Cl−5−Me−3−Py]、[2279:2−Me−5−Me−3−Py]、[2280:4−Me−5−Me−3−Py]、[2281:6−Me−5−Me−3−Py]、[2282:2−CF3−5−Me−3−Py]、[2283:4−CF3−5−Me−3−Py]、[2284:6−CF3−5−Me−3−Py]、[2285:2−CN−5−Me−3−Py]、[2286:4−CN−5−Me−3−Py]、[2287:6−CN−5−Me−3−Py]、[2288:2−OMe−5−Me−3−Py]、[2289:4−OMe−5−Me−3−Py]、[2290:6−OMe−5−Me−3−Py]、[2291:6−Me−3−Py]、[2292:2−Cl−6−Me−3−Py]、[2293:4−Cl−6−Me−3−Py]、[2294:5−Cl−6−Me−3−Py]、[2295:2−Me−6−Me−3−Py]、[2296:4−Me−6−Me−3−Py]、[2297:5−Me−6−Me−3−Py]、[2298:2−CF3−6−Me−3−Py]、[2299:4−CF3−6−Me−3−Py]、[2300:5−CF3−6−Me−3−Py]、 [2201: 6-Me-4-I-3-Py], [2202: 2-CF3-4-I-3-Py], [2203: 5-CF3-4-I-3-Py], [2204 : 6-CF3-4-I-3-Py], [2205: 2-CN-4-I-3-Py], [2206: 5-CN-4-I-3-Py], [2207: 6 -CN-4-I-3-Py], [2208: 2-OMe-4-I-3-Py], [2209: 5-OMe-4-I-3-Py], [2210: 6-OMe -4-I-3-Py], [2211: 5-I-3-Py], [2212: 2-Cl-5-I-3-Py], [2213: 4-Cl-5-I-3 -Py], [2214: 6-Cl-5-I-3-Py], [2215: 2-Me-5-I-3-Py], [2216: 4-Me-5-I-3- y], [2217: 6-Me-5-I-3-Py], [2218: 2-CF3-5-I-3-Py], [2219: 4-CF3-5-I-3-Py] [2220: 6-CF3-5-I-3-Py], [2221: 2-CN-5-I-3-Py], [2222: 4-CN-5-I-3-Py], [ 2223: 6-CN-5-I-3-Py], [2224: 2-OMe-5-I-3-Py], [2225: 4-OMe-5-I-3-Py], [2226: 6-OMe-5-I-3-Py], [2227: 6-I-3-Py], [2228: 2-Cl-6-I-3-Py], [2229: 4-Cl-6 I-3-Py], [2230: 5-Cl-6-I-3-Py], [2231: 2-Me-6-I-3-Py], [2232: 4-Me-6-6 -3-Py], [2233: 5-Me-6-I-3-Py], [2234: 2-CF3-6-I-3-Py], [2235: 4-CF3-6-I-3 -Py], [2236: 5-CF3-6-I-3-Py], [2237: 2-CN-6-I-3-Py], [2238: 4-CN-6-I-3-Py ], [2239: 5-CN-6-I-3-Py], [2240: 2-OMe-6-I-3-Py], [2241: 4-OMe-6-I-3-Py], [2242: 5-OMe-6-I-3-Py], [2243: 2-Me-3-Py], [2244: 4-Cl-2-Me-3-Py], [2245: 5-Cl -2-Me-3-Py], [2246: 6-Cl-2-Me-3-Py], [2247: 4-Me-2-Me-3-Py], [2248 : 5-Me-2-Me-3-Py], [2249: 6-Me-2-Me-3-Py], [2250: 4-CF3-2-Me-3-Py], [2251: 5 -CF3-2-Me-3-Py], [2252: 6-CF3-2-Me-3-Py], [2253: 4-CN-2-Me-3-Py], [2254: 5-CN -2-Me-3-Py], [2255: 6-CN-2-Me-3-Py], [2256: 4-OMe-2-Me-3-Py], [2257: 5-OMe-2 -Me-3-Py], [2258: 6-OMe-2-Me-3-Py], [2259: 4-Me-3-Py], [2260: 2-Cl-4-Me-3-Py ], [2261: 5-Cl-4-Me-3-Py], [2262: 6-Cl-4-Me-3-Py], [2263: 2 Me-4-Me-3-Py], [2264: 5-Me-4-Me-3-Py], [2265: 6-Me-4-Me-3-Py], [2266: 2-CF3- 4-Me-3-Py], [2267: 5-CF3-4-Me-3-Py], [2268: 6-CF3-4-Me-3-Py], [2269: 2-CN-4- Me-3-Py], [2270: 5-CN-4-Me-3-Py], [2271: 6-CN-4-Me-3-Py], [2272: 2-OMe-4-Me- 3-Py], [2273: 5-OMe-4-Me-3-Py], [2274: 6-OMe-4-Me-3-Py], [2275: 5-Me-3-Py], [ 2276: 2-Cl-5-Me-3-Py], [2277: 4-Cl-5-Me-3-Py], [2278: 6-C -5-Me-3-Py], [2279: 2-Me-5-Me-3-Py], [2280: 4-Me-5-Me-3-Py], [2281: 6-Me-5 -Me-3-Py], [2282: 2-CF3-5-Me-3-Py], [2283: 4-CF3-5-Me-3-Py], [2284: 6-CF3-5-Me -3-Py], [2285: 2-CN-5-Me-3-Py], [2286: 4-CN-5-Me-3-Py], [2287: 6-CN-5-Me-3. -Py], [2288: 2-OMe-5-Me-3-Py], [2289: 4-OMe-5-Me-3-Py], [2290: 6-OMe-5-Me-3-Py ], [2291: 6-Me-3-Py], [2292: 2-Cl-6-Me-3-Py], [2293: 4-Cl-6]. -Me-3-Py], [2294: 5-Cl-6-Me-3-Py], [2295: 2-Me-6-Me-3-Py], [2296: 4-Me-6-Me -3-Py], [2297: 5-Me-6-Me-3-Py], [2298: 2-CF3-6-Me-3-Py], [2299: 4-CF3-6-Me-3. -Py], [2300: 5-CF3-6-Me-3-Py],
[2301:2−CN−6−Me−3−Py]、[2302:4−CN−6−Me−3−Py]、[2303:5−CN−6−Me−3−Py]、[2304:2−OMe−6−Me−3−Py]、[2305:4−OMe−6−Me−3−Py]、[2306:5−OMe−6−Me−3−Py]、[2307:2−OMe−3−Py]、[2308:4−Cl−2−OMe−3−Py]、[2309:5−Cl−2−OMe−3−Py]、[2310:6−Cl−2−OMe−3−Py]、[2311:4−Me−2−OMe−3−Py]、[2312:5−Me−2−OMe−3−Py]、[2313:6−Me−2−OMe−3−Py]、[2314:4−CF3−2−OMe−3−Py]、[2315:5−CF3−2−OMe−3−Py]、[2316:6−CF3−2−OMe−3−Py]、[2317:4−CN−2−OMe−3−Py]、[2318:5−CN−2−OMe−3−Py]、[2319:6−CN−2−OMe−3−Py]、[2320:4−OMe−2−OMe−3−Py]、[2321:5−OMe−2−OMe−3−Py]、[2322:6−OMe−2−OMe−3−Py]、[2323:4−OMe−3−Py]、[2324:2−Cl−4−OMe−3−Py]、[2325:5−Cl−4−OMe−3−Py]、[2326:6−Cl−4−OMe−3−Py]、[2327:2−Me−4−OMe−3−Py]、[2328:5−Me−4−OMe−3−Py]、[2329:6−Me−4−OMe−3−Py]、[2330:2−CF3−4−OMe−3−Py]、[2331:5−CF3−4−OMe−3−Py]、[2332:6−CF3−4−OMe−3−Py]、[2333:2−CN−4−OMe−3−Py]、[2334:5−CN−4−OMe−3−Py]、[2335:6−CN−4−OMe−3−Py]、[2336:2−OMe−4−OMe−3−Py]、[2337:5−OMe−4−OMe−3−Py]、[2338:6−OMe−4−OMe−3−Py]、[2339:5−OMe−3−Py]、[2340:2−Cl−5−OMe−3−Py]、[2341:4−Cl−5−OMe−3−Py]、[2342:6−Cl−5−OMe−3−Py]、[2343:2−Me−5−OMe−3−Py]、[2344:4−Me−5−OMe−3−Py]、[2345:6−Me−5−OMe−3−Py]、[2346:2−CF3−5−OMe−3−Py]、[2347:4−CF3−5−OMe−3−Py]、[2348:6−CF3−5−OMe−3−Py]、[2349:2−CN−5−OMe−3−Py]、[2350:4−CN−5−OMe−3−Py]、[2351:6−CN−5−OMe−3−Py]、[2352:2−OMe−5−OMe−3−Py]、[2353:4−OMe−5−OMe−3−Py]、[2354:6−OMe−5−OMe−3−Py]、[2355:6−OMe−3−Py]、[2356:2−Cl−6−OMe−3−Py]、[2357:4−Cl−6−OMe−3−Py]、[2358:5−Cl−6−OMe−3−Py]、[2359:2−Me−6−OMe−3−Py]、[2360:4−Me−6−OMe−3−Py]、[2361:5−Me−6−OMe−3−Py]、[2362:2−CF3−6−OMe−3−Py]、[2363:4−CF3−6−OMe−3−Py]、[2364:5−CF3−6−OMe−3−Py]、[2365:2−CN−6−OMe−3−Py]、[2366:4−CN−6−OMe−3−Py]、[2367:5−CN−6−OMe−3−Py]、[2368:2−OMe−6−OMe−3−Py]、[2369:4−OMe−6−OMe−3−Py]、[2370:5−OMe−6−OMe−3−Py]、[2371:2−CF3−3−Py]、[2372:4−Cl−2−CF3−3−Py]、[2373:5−Cl−2−CF3−3−Py]、[2374:6−Cl−2−CF3−3−Py]、[2375:4−Me−2−CF3−3−Py]、[2376:5−Me−2−CF3−3−Py]、[2377:6−Me−2−CF3−3−Py]、[2378:4−CF3−2−CF3−3−Py]、[2379:5−CF3−2−CF3−3−Py]、[2380:6−CF3−2−CF3−3−Py]、[2381:4−CN−2−CF3−3−Py]、[2382:5−CN−2−CF3−3−Py]、[2383:6−CN−2−CF3−3−Py]、[2384:4−OMe−2−CF3−3−Py]、[2385:5−OMe−2−CF3−3−Py]、[2386:6−OMe−2−CF3−3−Py]、[2387:4−CF3−3−Py]、[2388:2−Cl−4−CF3−3−Py]、[2389:5−Cl−4−CF3−3−Py]、[2390:6−Cl−4−CF3−3−Py]、[2391:2−Me−4−CF3−3−Py]、[2392:5−Me−4−CF3−3−Py]、[2393:6−Me−4−CF3−3−Py]、[2394:2−CF3−4−CF3−3−Py]、[2395:5−CF3−4−CF3−3−Py]、[2396:6−CF3−4−CF3−3−Py]、[2397:2−CN−4−CF3−3−Py]、[2398:5−CN−4−CF3−3−Py]、[2399:6−CN−4−CF3−3−Py]、[2400:2−OMe−4−CF3−3−Py]、 [2301: 2-CN-6-Me-3-Py], [2302: 4-CN-6-Me-3-Py], [2303: 5-CN-6-Me-3-Py], [2304 : 2-OMe-6-Me-3-Py], [2305: 4-OMe-6-Me-3-Py], [2306: 5-OMe-6-Me-3-Py], [2307: 2 -OMe-3-Py], [2308: 4-Cl-2-OMe-3-Py], [2309: 5-Cl-2-OMe-3-Py], [2310: 6-Cl-2-OMe -3-Py], [2311: 4-Me-2-OMe-3-Py], [2312: 5-Me-2-OMe-3-Py], [2313: 6-Me-2-OMe-3 -Py], [2314: 4-CF3-2-OMe-3-Py], [2315: 5-CF3-2-OMe- -Py], [2316: 6-CF3-2-OMe-3-Py], [2317: 4-CN-2-OMe-3-Py], [2318: 5-CN-2-OMe-3-Py] ], [2319: 6-CN-2-OMe-3-Py], [2320: 4-OMe-2-OMe-3-Py], [2321: 5-OMe-2-OMe-3-Py], [2322: 6-OMe-2-OMe-3-Py], [2323: 4-OMe-3-Py], [2324: 2-Cl-4-OMe-3-Py], [2325: 5-Cl -4-OMe-3-Py], [2326: 6-Cl-4-OMe-3-Py], [2327: 2-Me-4-OMe-3-Py], [2328: 5-Me-4 -OMe-3-Py], [2329: 6-Me-4-OMe-3-Py], [2330: -CF3-4-OMe-3-Py], [2331: 5-CF3-4-OMe-3-Py], [2332: 6-CF3-4-OMe-3-Py], [2333: 2-CN -4-OMe-3-Py], [2334: 5-CN-4-OMe-3-Py], [2335: 6-CN-4-OMe-3-Py], [2336: 2-OMe-4 -OMe-3-Py], [2337: 5-OMe-4-OMe-3-Py], [2338: 6-OMe-4-OMe-3-Py], [2339: 5-OMe-3-Py] ], [2340: 2-Cl-5-OMe-3-Py], [2341: 4-Cl-5-OMe-3-Py], [2342: 6-Cl-5-OMe-3-Py], [2343: 2-Me-5-OMe-3-Py], [2344: 4-Me-5-OMe- 3-Py], [2345: 6-Me-5-OMe-3-Py], [2346: 2-CF3-5-OMe-3-Py], [2347: 4-CF3-5-OMe-3- Py], [2348: 6-CF3-5-OMe-3-Py], [2349: 2-CN-5-OMe-3-Py], [2350: 4-CN-5-OMe-3-Py] , [2351: 6-CN-5-OMe-3-Py], [2352: 2-OMe-5-OMe-3-Py], [2353: 4-OMe-5-OMe-3-Py], [ 2354: 6-OMe-5-OMe-3-Py], [2355: 6-OMe-3-Py], [2356: 2-Cl-6-OMe-3-Py], [2357: 4-Cl- 6-OMe-3-Py], [2358: 5-Cl-6-OMe-3-Py], [235 : 2-Me-6-OMe-3-Py], [2360: 4-Me-6-OMe-3-Py], [2361: 5-Me-6-OMe-3-Py], [2362: 2 -CF3-6-OMe-3-Py], [2363: 4-CF3-6-OMe-3-Py], [2364: 5-CF3-6-OMe-3-Py], [2365: 2-CN -6-OMe-3-Py], [2366: 4-CN-6-OMe-3-Py], [2367: 5-CN-6-OMe-3-Py], [2368: 2-OMe-6 -OMe-3-Py], [2369: 4-OMe-6-OMe-3-Py], [2370: 5-OMe-6-OMe-3-Py], [2371: 2-CF3-3-Py] ], [2372: 4-Cl-2-CF3-3-Py], [2373: 5-Cl-2-C 3-3-Py], [2374: 6-Cl-2-CF3-3-Py], [2375: 4-Me-2-CF3-3-Py], [2376: 5-Me-2-CF3- 3-Py], [2377: 6-Me-2-CF3-3-Py], [2378: 4-CF3-2-CF3-3-Py], [2379: 5-CF3-2-CF3-3 Py], [2380: 6-CF3-2-CF3-3-Py], [2381: 4-CN-2-CF3-3-Py], [2382: 5-CN-2-CF3-3-Py] [2383: 6-CN-2-CF3-3-Py], [2384: 4-OMe-2-CF3-3-Py], [2385: 5-OMe-2-CF3-3-Py], [ 2386: 6-OMe-2-CF3-3-Py], [2387: 4-CF3-3-Py], [2 388: 2-Cl-4-CF3-3-Py], [2389: 5-Cl-4-CF3-3-Py], [2390: 6-Cl-4-CF3-3-Py], [2391: 2-Me-4-CF3-3-Py], [2392: 5-Me-4-CF3-3-Py], [2393: 6-Me-4-CF3-3-Py], [2394: 2- CF3-4-CF3-3-Py], [2395: 5-CF3-4-CF3-3-Py], [2396: 6-CF3-4-CF3-3-Py], [2397: 2-CN- 4-CF3-3-Py], [2398: 5-CN-4-CF3-3-Py], [2399: 6-CN-4-CF3-3-Py], [2400: 2-OMe-4- CF3-3-Py],
[2401:5−OMe−4−CF3−3−Py]、[2402:6−OMe−4−CF3−3−Py]、[2403:5−CF3−3−Py]、[2404:2−Cl−5−CF3−3−Py]、[2405:4−Cl−5−CF3−3−Py]、[2406:6−Cl−5−CF3−3−Py]、[2407:2−Me−5−CF3−3−Py]、[2408:4−Me−5−CF3−3−Py]、[2409:6−Me−5−CF3−3−Py]、[2410:2−CF3−5−CF3−3−Py]、[2411:4−CF3−5−CF3−3−Py]、[2412:6−CF3−5−CF3−3−Py]、[2413:2−CN−5−CF3−3−Py]、[2414:4−CN−5−CF3−3−Py]、[2415:6−CN−5−CF3−3−Py]、[2416:2−OMe−5−CF3−3−Py]、[2417:4−OMe−5−CF3−3−Py]、[2418:6−OMe−5−CF3−3−Py]、[2419:6−CF3−3−Py]、[2420:2−Cl−6−CF3−3−Py]、[2421:4−Cl−6−CF3−3−Py]、[2422:5−Cl−6−CF3−3−Py]、[2423:2−Me−6−CF3−3−Py]、[2424:4−Me−6−CF3−3−Py]、[2425:5−Me−6−CF3−3−Py]、[2426:2−CF3−6−CF3−3−Py]、[2427:4−CF3−6−CF3−3−Py]、[2428:5−CF3−6−CF3−3−Py]、[2429:2−CN−6−CF3−3−Py]、[2430:4−CN−6−CF3−3−Py]、[2431:5−CN−6−CF3−3−Py]、[2432:2−OMe−6−CF3−3−Py]、[2433:4−OMe−6−CF3−3−Py]、[2434:5−OMe−6−CF3−3−Py]、[2435:2−OCF3−3−Py]、[2436:4−Cl−2−OCF3−3−Py]、[2437:5−Cl−2−OCF3−3−Py]、[2438:6−Cl−2−OCF3−3−Py]、[2439:4−Me−2−OCF3−3−Py]、[2440:5−Me−2−OCF3−3−Py]、[2441:6−Me−2−OCF3−3−Py]、[2442:4−CF3−2−OCF3−3−Py]、[2443:5−CF3−2−OCF3−3−Py]、[2444:6−CF3−2−OCF3−3−Py]、[2445:4−CN−2−OCF3−3−Py]、[2446:5−CN−2−OCF3−3−Py]、[2447:6−CN−2−OCF3−3−Py]、[2448:4−OMe−2−OCF3−3−Py]、[2449:5−OMe−2−OCF3−3−Py]、[2450:6−OMe−2−OCF3−3−Py]、[2451:4−OCF3−3−Py]、[2452:2−Cl−4−OCF3−3−Py]、[2453:5−Cl−4−OCF3−3−Py]、[2454:6−Cl−4−OCF3−3−Py]、[2455:2−Me−4−OCF3−3−Py]、[2456:5−Me−4−OCF3−3−Py]、[2457:6−Me−4−OCF3−3−Py]、[2458:2−CF3−4−OCF3−3−Py]、[2459:5−CF3−4−OCF3−3−Py]、[2460:6−CF3−4−OCF3−3−Py]、[2461:2−CN−4−OCF3−3−Py]、[2462:5−CN−4−OCF3−3−Py]、[2463:6−CN−4−OCF3−3−Py]、[2464:2−OMe−4−OCF3−3−Py]、[2465:5−OMe−4−OCF3−3−Py]、[2466:6−OMe−4−OCF3−3−Py]、[2467:5−OCF3−3−Py]、[2468:2−Cl−5−OCF3−3−Py]、[2469:4−Cl−5−OCF3−3−Py]、[2470:6−Cl−5−OCF3−3−Py]、[2471:2−Me−5−OCF3−3−Py]、[2472:4−Me−5−OCF3−3−Py]、[2473:6−Me−5−OCF3−3−Py]、[2474:2−CF3−5−OCF3−3−Py]、[2475:4−CF3−5−OCF3−3−Py]、[2476:6−CF3−5−OCF3−3−Py]、[2477:2−CN−5−OCF3−3−Py]、[2478:4−CN−5−OCF3−3−Py]、[2479:6−CN−5−OCF3−3−Py]、[2480:2−OMe−5−OCF3−3−Py]、[2481:4−OMe−5−OCF3−3−Py]、[2482:6−OMe−5−OCF3−3−Py]、[2483:6−OCF3−3−Py]、[2484:2−Cl−6−OCF3−3−Py]、[2485:4−Cl−6−OCF3−3−Py]、[2486:5−Cl−6−OCF3−3−Py]、[2487:2−Me−6−OCF3−3−Py]、[2488:4−Me−6−OCF3−3−Py]、[2489:5−Me−6−OCF3−3−Py]、[2490:2−CF3−6−OCF3−3−Py]、[2491:4−CF3−6−OCF3−3−Py]、[2492:5−CF3−6−OCF3−3−Py]、[2493:2−CN−6−OCF3−3−Py]、[2494:4−CN−6−OCF3−3−Py]、[2495:5−CN−6−OCF3−3−Py]、[2496:2−OMe−6−OCF3−3−Py]、[2497:4−OMe−6−OCF3−3−Py]、[2498:5−OMe−6−OCF3−3−Py]、[2499:2−CHF2−3−Py]、[2500:4−Cl−2−CHF2−3−Py]、 [2401: 5-OMe-4-CF3-3-Py], [2402: 6-OMe-4-CF3-3-Py], [2403: 5-CF3-3-Py], [2404: 2-Cl -5-CF3-3-Py], [2405: 4-Cl-5-CF3-3-Py], [2406: 6-Cl-5-CF3-3-Py], [2407: 2-Me-5. -CF3-3-Py], [2408: 4-Me-5-CF3-3-Py], [2409: 6-Me-5-CF3-3-Py], [2410: 2-CF3-5-CF3 -3-Py], [2411: 4-CF3-5-CF3-3-Py], [2412: 6-CF3-5-CF3-3-Py], [2413: 2-CN-5-CF3-3) -Py], [2414: 4-CN-5-CF3-3-Py], [2415: 6-CN- -CF3-3-Py], [2416: 2-OMe-5-CF3-3-Py], [2417: 4-OMe-5-CF3-3-Py], [2418: 6-OMe-5-CF3 -3-Py], [2419: 6-CF3-3-Py], [2420: 2-Cl-6-CF3-3-Py], [2421: 4-Cl-6-CF3-3-Py], [2422: 5-Cl-6-CF3-3-Py], [2423: 2-Me-6-CF3-3-Py], [2424: 4-Me-6-CF3-3-Py], [2425 : 5-Me-6-CF3-3-Py], [2426: 2-CF3-6-CF3-3-Py], [2427: 4-CF3-6-CF3-3-Py], [2428: 5 -CF3-6-CF3-3-Py], [2429: 2-CN-6-CF3-3-Py [2430: 4-CN-6-CF3-3-Py], [2431: 5-CN-6-CF3-3-Py], [2432: 2-OMe-6-CF3-3-Py], [ 2433: 4-OMe-6-CF3-3-Py], [2434: 5-OMe-6-CF3-3-Py], [2435: 2-OCF3-3-Py], [2436: 4-Cl- 2-OCF3-3-Py], [2437: 5-Cl-2-OCF3-3-Py], [2438: 6-Cl-2-OCF3-3-Py], [2439: 4-Me-2-] OCF3-3-Py], [2440: 5-Me-2-OCF3-3-Py], [2441: 6-Me-2-OCF3-3-Py], [2442: 4-CF3-2-OCF3- 3-Py], [2443: 5-CF3-2-OCF3-3-Py], [ 2444: 6-CF3-2-OCF3-3-Py], [2445: 4-CN-2-OCF3-3-Py], [2446: 5-CN-2-OCF3-3-Py], [2447: 6-CN-2-OCF3-3-Py], [2448: 4-OMe-2-OCF3-3-Py], [2449: 5-OMe-2-OCF3-3-Py], [2450: 6- OMe-2-OCF3-3-Py], [2451: 4-OCF3-3-Py], [2452: 2-Cl-4-OCF3-3-Py], [2453: 5-Cl-4-OCF3- 3-Py], [2454: 6-Cl-4-OCF3-3-Py], [2455: 2-Me-4-OCF3-3-Py], [2456: 5-Me-4-OCF3-3 Py], [2457: 6-Me-4-OCF3-3-Py] [2458: 2-CF3-4-OCF3-3-Py], [2259: 5-CF3-4-OCF3-3-Py], [2460: 6-CF3-4-OCF3-3-Py], [2461 : 2-CN-4-OCF3-3-Py], [2462: 5-CN-4-OCF3-3-Py], [2463: 6-CN-4-OCF3-3-Py], [2464: 2] -OMe-4-OCF3-3-Py], [2465: 5-OMe-4-OCF3-3-Py], [2466: 6-OMe-4-OCF3-3-Py], [2467: 5-OCF3 -3-Py], [2468: 2-Cl-5-OCF3-3-Py], [2469: 4-Cl-5-OCF3-3-Py], [2470: 6-Cl-5-OCF3-3. -Py], [2471: 2-Me-5-OCF3-3. Py], [2472: 4-Me-5-OCF3-3-Py], [2473: 6-Me-5-OCF3-3-Py], [2474: 2-CF3-5-OCF3-3-Py] [2475: 4-CF3-5-OCF3-3-Py], [2476: 6-CF3-5-OCF3-3-Py], [2477: 2-CN-5-OCF3-3-Py], [ 2478: 4-CN-5-OCF3-3-Py], [2479: 6-CN-5-OCF3-3-Py], [2480: 2-OMe-5-OCF3-3-Py], [2481: 4-OMe-5-OCF3-3-Py], [2482: 6-OMe-5-OCF3-3-Py], [2483: 6-OCF3-3-Py], [2484: 2-Cl-6 OCF3-3-Py], [2485: 4-Cl-6-OCF 3-3-3-Py], [2486: 5-Cl-6-OCF3-3-Py], [2487: 2-Me-6-OCF3-3-Py], [2488: 4-Me-6-OCF3- 3-Py], [2489: 5-Me-6-OCF3-3-Py], [2490: 2-CF3-6-OCF3-3-Py], [2491: 4-CF3-6-OCF3-3- Py], [2492: 5-CF3-6-OCF3-3-Py], [2493: 2-CN-6-OCF3-3-Py], [2494: 4-CN-6-OCF3-3-Py] [2495: 5-CN-6-OCF3-3-Py], [2496: 2-OMe-6-OCF3-3-Py], [2497: 4-OMe-6-OCF3-3-Py], [ 2498: 5-OMe-6-OCF3-3-Py], [2499: 2 CHF2-3-Py], [2500: 4-Cl-2-CHF2-3-Py],
[2501:5−Cl−2−CHF2−3−Py]、[2502:6−Cl−2−CHF2−3−Py]、[2503:4−Me−2−CHF2−3−Py]、[2504:5−Me−2−CHF2−3−Py]、[2505:6−Me−2−CHF2−3−Py]、[2506:4−CF3−2−CHF2−3−Py]、[2507:5−CF3−2−CHF2−3−Py]、[2508:6−CF3−2−CHF2−3−Py]、[2509:4−CN−2−CHF2−3−Py]、[2510:5−CN−2−CHF2−3−Py]、[2511:6−CN−2−CHF2−3−Py]、[2512:4−OMe−2−CHF2−3−Py]、[2513:5−OMe−2−CHF2−3−Py]、[2514:6−OMe−2−CHF2−3−Py]、[2515:4−CHF2−3−Py]、[2516:2−Cl−4−CHF2−3−Py]、[2517:5−Cl−4−CHF2−3−Py]、[2518:6−Cl−4−CHF2−3−Py]、[2519:2−Me−4−CHF2−3−Py]、[2520:5−Me−4−CHF2−3−Py]、[2521:6−Me−4−CHF2−3−Py]、[2522:2−CF3−4−CHF2−3−Py]、[2523:5−CF3−4−CHF2−3−Py]、[2524:6−CF3−4−CHF2−3−Py]、[2525:2−CN−4−CHF2−3−Py]、[2526:5−CN−4−CHF2−3−Py]、[2527:6−CN−4−CHF2−3−Py]、[2528:2−OMe−4−CHF2−3−Py]、[2529:5−OMe−4−CHF2−3−Py]、[2530:6−OMe−4−CHF2−3−Py]、[2531:5−CHF2−3−Py]、[2532:2−Cl−5−CHF2−3−Py]、[2533:4−Cl−5−CHF2−3−Py]、[2534:6−Cl−5−CHF2−3−Py]、[2535:2−Me−5−CHF2−3−Py]、[2536:4−Me−5−CHF2−3−Py]、[2537:6−Me−5−CHF2−3−Py]、[2538:2−CF3−5−CHF2−3−Py]、[2539:4−CF3−5−CHF2−3−Py]、[2540:6−CF3−5−CHF2−3−Py]、[2541:2−CN−5−CHF2−3−Py]、[2542:4−CN−5−CHF2−3−Py]、[2543:6−CN−5−CHF2−3−Py]、[2544:2−OMe−5−CHF2−3−Py]、[2545:4−OMe−5−CHF2−3−Py]、[2546:6−OMe−5−CHF2−3−Py]、[2547:6−CHF2−3−Py]、[2548:2−Cl−6−CHF2−3−Py]、[2549:4−Cl−6−CHF2−3−Py]、[2550:5−Cl−6−CHF2−3−Py]、[2551:2−Me−6−CHF2−3−Py]、[2552:4−Me−6−CHF2−3−Py]、[2553:5−Me−6−CHF2−3−Py]、[2554:2−CF3−6−CHF2−3−Py]、[2555:4−CF3−6−CHF2−3−Py]、[2556:5−CF3−6−CHF2−3−Py]、[2557:2−CN−6−CHF2−3−Py]、[2558:4−CN−6−CHF2−3−Py]、[2559:5−CN−6−CHF2−3−Py]、[2560:2−OMe−6−CHF2−3−Py]、[2561:4−OMe−6−CHF2−3−Py]、[2562:5−OMe−6−CHF2−3−Py]、[2563:2−OCHF2−3−Py]、[2564:4−Cl−2−OCHF2−3−Py]、[2565:5−Cl−2−OCHF2−3−Py]、[2566:6−Cl−2−OCHF2−3−Py]、[2567:4−Me−2−OCHF2−3−Py]、[2568:5−Me−2−OCHF2−3−Py]、[2569:6−Me−2−OCHF2−3−Py]、[2570:4−CF3−2−OCHF2−3−Py]、[2571:5−CF3−2−OCHF2−3−Py]、[2572:6−CF3−2−OCHF2−3−Py]、[2573:4−CN−2−OCHF2−3−Py]、[2574:5−CN−2−OCHF2−3−Py]、[2575:6−CN−2−OCHF2−3−Py]、[2576:4−OMe−2−OCHF2−3−Py]、[2577:5−OMe−2−OCHF2−3−Py]、[2578:6−OMe−2−OCHF2−3−Py]、[2579:4−OCHF2−3−Py]、[2580:2−Cl−4−OCHF2−3−Py]、[2581:5−Cl−4−OCHF2−3−Py]、[2582:6−Cl−4−OCHF2−3−Py]、[2583:2−Me−4−OCHF2−3−Py]、[2584:5−Me−4−OCHF2−3−Py]、[2585:6−Me−4−OCHF2−3−Py]、[2586:2−CF3−4−OCHF2−3−Py]、[2587:5−CF3−4−OCHF2−3−Py]、[2588:6−CF3−4−OCHF2−3−Py]、[2589:2−CN−4−OCHF2−3−Py]、[2590:5−CN−4−OCHF2−3−Py]、[2591:6−CN−4−OCHF2−3−Py]、[2592:2−OMe−4−OCHF2−3−Py]、[2593:5−OMe−4−OCHF2−3−Py]、[2594:6−OMe−4−OCHF2−3−Py]、[2595:5−OCHF2−3−Py]、[2596:2−Cl−5−OCHF2−3−Py]、[2597:4−Cl−5−OCHF2−3−Py]、[2598:6−Cl−5−OCHF2−3−Py]、[2599:2−Me−5−OCHF2−3−Py]、[2600:4−Me−5−OCHF2−3−Py]、 [2501: 5-Cl-2-CHF2-3-Py], [2502: 6-Cl-2-CHF2-3-Py], [2503: 4-Me-2-CHF2-3-Py], [2504 : 5-Me-2-CHF2-3-Py], [2505: 6-Me-2-CHF2-3-Py], [2506: 4-CF3-2-CHF2-3-Py], [2507: 5 -CF3-2-CHF2-3-Py], [2508: 6-CF3-2-CHF2-3-Py], [2509: 4-CN-2-CHF2-3-Py], [2510: 5-CN -2-CHF2-3-Py], [2511: 6-CN-2-CHF2-3-Py], [2512: 4-OMe-2-CHF2-3-Py], [2513: 5-OMe-2 -CHF2-3-Py], [2514: 6-OMe-2-CH 2-3-Py], [2515: 4-CHF2-3-Py], [2516: 2-Cl-4-CHF2-3-Py], [2517: 5-Cl-4-CHF2-3-Py] [2518: 6-Cl-4-CHF2-3-Py], [2519: 2-Me-4-CHF2-3-Py], [2520: 5-Me-4-CHF2-3-Py], [ 2521: 6-Me-4-CHF2-3-Py], [2522: 2-CF3-4-CHF2-3-Py], [2523: 5-CF3-4-CHF2-3-Py], [2524: 6-CF3-4-CHF2-3-Py], [2525: 2-CN-4-CHF2-3-Py], [2526: 5-CN-4-CHF2-3-Py], [2527: 6- CN-4-CHF2-3-Py], [2528: 2-OMe-4- HF2-3-Py], [2529: 5-OMe-4-CHF2-3-Py], [2530: 6-OMe-4-CHF2-3-Py], [2531: 5-CHF2-3-Py] [2532: 2-Cl-5-CHF2-3-Py], [2533: 4-Cl-5-CHF2-3-Py], [2534: 6-Cl-5-CHF2-3-Py], [ 2535: 2-Me-5-CHF2-3-Py], [2536: 4-Me-5-CHF2-3-Py], [2537: 6-Me-5-CHF2-3-Py], [2538: 2-CF3-5-CHF2-3-Py], [2539: 4-CF3-5-CHF2-3-Py], [2540: 6-CF3-5-CHF2-3-Py], [2541: 2- CN-5-CHF2-3-Py], [2542: 4-CN- 5-CHF2-3-Py], [2543: 6-CN-5-CHF2-3-Py], [2544: 2-OMe-5-CHF2-3-Py], [2545: 4-OMe-5 CHF2-3-Py], [2546: 6-OMe-5-CHF2-3-Py], [2547: 6-CHF2-3-Py], [2548: 2-Cl-6-CHF2-3-Py] [2549: 4-Cl-6-CHF2-3-Py], [2550: 5-Cl-6-CHF2-3-Py], [2551: 2-Me-6-CHF2-3-Py], [ 2552: 4-Me-6-CHF2-3-Py], [2553: 5-Me-6-CHF2-3-Py], [2554: 2-CF3-6-CHF2-3-Py], [2555: 4-CF3-6-CHF2-3-Py], [2556: 5- F3-6-CHF2-3-Py], [2557: 2-CN-6-CHF2-3-Py], [2558: 4-CN-6-CHF2-3-Py], [2559: 5-CN- 6-CHF2-3-Py], [2560: 2-OMe-6-CHF2-3-Py], [2561: 4-OMe-6-CHF2-3-Py], [2562: 5-OMe-6 CHF2-3-Py], [2563: 2-OCHF2-3-Py], [2564: 4-Cl-2-OCHF2-3-Py], [2565: 5-Cl-2-OCHF2-3-Py] [2566: 6-Cl-2-OCHF2-3-Py], [2567: 4-Me-2-OCHF2-3-Py], [2568: 5-Me-2-OCHF2-3-Py], [ 2569: 6-Me-2-OCHF2-3-Py] [2570: 4-CF3-2-OCHF2-3-Py], [2571: 5-CF3-2-OCHF2-3-Py], [2572: 6-CF3-2-OCHF2-3-Py], [2573 : 4-CN-2-OCHF2-3-Py], [2574: 5-CN-2-OCHF2-3-Py], [2575: 6-CN-2-OCHF2-3-Py], [2576: 4 -OMe-2-OCHF2-3-Py], [2577: 5-OMe-2-OCHF2-3-Py], [2578: 6-OMe-2-OCHF2-3-Py], [2579: 4-OCHF2 -3-Py], [2580: 2-Cl-4-OCHF2-3-Py], [2581: 5-Cl-4-OCHF2-3-Py], [2582: 6-Cl-4-OCHF2-3 -Py], [2583: 2 -Me-4-OCHF2-3-Py], [2584: 5-Me-4-OCHF2-3-Py], [2585: 6-Me-4-OCHF2-3-Py], [2586: 2-CF3 -4-OCHF2-3-Py], [2588: 5-CF3-4-OCHF2-3-Py], [2588: 6-CF3-4-OCHF2-3-Py], [2589: 2-CN-4 -OCHF2-3-Py], [2590: 5-CN-4-OCHF2-3-Py], [2591: 6-CN-4-OCHF2-3-Py], [2592: 2-OMe-4-OCHF2 -3-Py], [2593: 5-OMe-4-OCHF2-3-Py], [2594: 6-OMe-4-OCHF2-3-Py], [2595: 5-OCHF2-3-Py], [2596: 2-Cl-5-O HF2-3-Py], [2597: 4-Cl-5-OCHF2-3-Py], [2598: 6-Cl-5-OCHF2-3-Py], [2599: 2-Me-5-OCHF2- 3-Py], [2600: 4-Me-5-OCHF2-3-Py],
[2601:6−Me−5−OCHF2−3−Py]、[2602:2−CF3−5−OCHF2−3−Py]、[2603:4−CF3−5−OCHF2−3−Py]、[2604:6−CF3−5−OCHF2−3−Py]、[2605:2−CN−5−OCHF2−3−Py]、[2606:4−CN−5−OCHF2−3−Py]、[2607:6−CN−5−OCHF2−3−Py]、[2608:2−OMe−5−OCHF2−3−Py]、[2609:4−OMe−5−OCHF2−3−Py]、[2610:6−OMe−5−OCHF2−3−Py]、[2611:6−OCHF2−3−Py]、[2612:2−Cl−6−OCHF2−3−Py]、[2613:4−Cl−6−OCHF2−3−Py]、[2614:5−Cl−6−OCHF2−3−Py]、[2615:2−Me−6−OCHF2−3−Py]、[2616:4−Me−6−OCHF2−3−Py]、[2617:5−Me−6−OCHF2−3−Py]、[2618:2−CF3−6−OCHF2−3−Py]、[2619:4−CF3−6−OCHF2−3−Py]、[2620:5−CF3−6−OCHF2−3−Py]、[2621:2−CN−6−OCHF2−3−Py]、[2622:4−CN−6−OCHF2−3−Py]、[2623:5−CN−6−OCHF2−3−Py]、[2624:2−OMe−6−OCHF2−3−Py]、[2625:4−OMe−6−OCHF2−3−Py]、[2626:5−OMe−6−OCHF2−3−Py]、[2627:2−Et−3−Py]、[2628:4−Cl−2−Et−3−Py]、[2629:5−Cl−2−Et−3−Py]、[2630:6−Cl−2−Et−3−Py]、[2631:4−Me−2−Et−3−Py]、[2632:5−Me−2−Et−3−Py]、[2633:6−Me−2−Et−3−Py]、[2634:4−CF3−2−Et−3−Py]、[2635:5−CF3−2−Et−3−Py]、[2636:6−CF3−2−Et−3−Py]、[2637:4−CN−2−Et−3−Py]、[2638:5−CN−2−Et−3−Py]、[2639:6−CN−2−Et−3−Py]、[2640:4−OMe−2−Et−3−Py]、[2641:5−OMe−2−Et−3−Py]、[2642:6−OMe−2−Et−3−Py]、[2643:4−Et−3−Py]、[2644:2−Cl−4−Et−3−Py]、[2645:5−Cl−4−Et−3−Py]、[2646:6−Cl−4−Et−3−Py]、[2647:2−Me−4−Et−3−Py]、[2648:5−Me−4−Et−3−Py]、[2649:6−Me−4−Et−3−Py]、[2650:2−CF3−4−Et−3−Py]、[2651:5−CF3−4−Et−3−Py]、[2652:6−CF3−4−Et−3−Py]、[2653:2−CN−4−Et−3−Py]、[2654:5−CN−4−Et−3−Py]、[2655:6−CN−4−Et−3−Py]、[2656:2−OMe−4−Et−3−Py]、[2657:5−OMe−4−Et−3−Py]、[2658:6−OMe−4−Et−3−Py]、[2659:5−Et−3−Py]、[2660:2−Cl−5−Et−3−Py]、[2661:4−Cl−5−Et−3−Py]、[2662:6−Cl−5−Et−3−Py]、[2663:2−Me−5−Et−3−Py]、[2664:4−Me−5−Et−3−Py]、[2665:6−Me−5−Et−3−Py]、[2666:2−CF3−5−Et−3−Py]、[2667:4−CF3−5−Et−3−Py]、[2668:6−CF3−5−Et−3−Py]、[2669:2−CN−5−Et−3−Py]、[2670:4−CN−5−Et−3−Py]、[2671:6−CN−5−Et−3−Py]、[2672:2−OMe−5−Et−3−Py]、[2673:4−OMe−5−Et−3−Py]、[2674:6−OMe−5−Et−3−Py]、[2675:6−Et−3−Py]、[2676:2−Cl−6−Et−3−Py]、[2677:4−Cl−6−Et−3−Py]、[2678:5−Cl−6−Et−3−Py]、[2679:2−Me−6−Et−3−Py]、[2680:4−Me−6−Et−3−Py]、[2681:5−Me−6−Et−3−Py]、[2682:2−CF3−6−Et−3−Py]、[2683:4−CF3−6−Et−3−Py]、[2684:5−CF3−6−Et−3−Py]、[2685:2−CN−6−Et−3−Py]、[2686:4−CN−6−Et−3−Py]、[2687:5−CN−6−Et−3−Py]、[2688:2−OMe−6−Et−3−Py]、[2689:4−OMe−6−Et−3−Py]、[2690:5−OMe−6−Et−3−Py]、[2691:2−CH2CF3−3−Py]、[2692:4−Cl−2−CH2CF3−3−Py]、[2693:5−Cl−2−CH2CF3−3−Py]、[2694:6−Cl−2−CH2CF3−3−Py]、[2695:4−Me−2−CH2CF3−3−Py]、[2696:5−Me−2−CH2CF3−3−Py]、[2697:6−Me−2−CH2CF3−3−Py]、[2698:4−CF3−2−CH2CF3−3−Py]、[2699:5−CF3−2−CH2CF3−3−Py]、[2700:6−CF3−2−CH2CF3−3−Py]、 [2601: 6-Me-5-OCHF2-3-Py], [2602: 2-CF3-5-OCHF2-3-Py], [2603: 4-CF3-5-OCHF2-3-Py], [2604] : 6-CF3-5-OCHF2-3-Py], [2605: 2-CN-5-OCHF2-3-Py], [2606: 4-CN-5-OCHF2-3-Py], [2607: 6 -CN-5-OCHF2-3-Py], [2608: 2-OMe-5-OCHF2-3-Py], [2609: 4-OMe-5-OCHF2-3-Py], [2610: 6-OMe -5-OCHF2-3-Py], [2611: 6-OCHF2-3-Py], [2612: 2-Cl-6-OCHF2-3-Py], [2613: 4-Cl-6-OCHF2-3 -Py], [2614: 5 Cl-6-OCHF2-3-Py], [2615: 2-Me-6-OCHF2-3-Py], [2616: 4-Me-6-OCHF2-3-Py], [2617: 5-Me- 6-OCHF2-3-Py], [2618: 2-CF3-6-OCHF2-3-Py], [2619: 4-CF3-6-OCHF2-3-Py], [2620: 5-CF3-6 OCHF2-3-Py], [2621: 2-CN-6-OCHF2-3-Py], [2622: 4-CN-6-OCHF2-3-Py], [2623: 5-CN-6-OCHF2- 3-Py], [2624: 2-OMe-6-OCHF2-3-Py], [2625: 4-OMe-6-OCHF2-3-Py], [2626: 5-OMe-6-OCHF2-3- Py], [2627: 2-E -3-Py], [2628: 4-Cl-2-Et-3-Py], [2629: 5-Cl-2-Et-3-Py], [2630: 6-Cl-2-Et-3 -Py], [2631: 4-Me-2-Et-3-Py], [2632: 5-Me-2-Et-3-Py], [2633: 6-Me-2-Et-3-Py] ], [2634: 4-CF3-2-Et-3-Py], [2635: 5-CF3-2-Et-3-Py], [2636: 6-CF3-2-Et-3-Py], [2638: 4-CN-2-Et-3-Py], [2638: 5-CN-2-Et-3-Py], [2539: 6-CN-2-Et-3-Py], [2640 : 4-OMe-2-Et-3-Py], [2641: 5-OMe-2-Et-3-Py], [2642: 6-OMe-2 -Et-3-Py], [2643: 4-Et-3-Py], [2644: 2-Cl-4-Et-3-Py], [2645: 5-Cl-4-Et-3-Py] ], [2646: 6-Cl-4-Et-3-Py], [2647: 2-Me-4-Et-3-Py], [2648: 5-Me-4-Et-3-Py], [2649: 6-Me-4-Et-3-Py], [2650: 2-CF3-4-Et-3-Py], [2651: 5-CF3-4-Et-3-Py], [2652] : 6-CF3-4-Et-3-Py], [2653: 2-CN-4-Et-3-Py], [2654: 5-CN-4-Et-3-Py], [2655: 6 -CN-4-Et-3-Py], [2656: 2-OMe-4-Et-3-Py], [2657: 5-OMe-4-Et 3-Py], [2658: 6-OMe-4-Et-3-Py], [2659: 5-Et-3-Py], [2660: 2-Cl-5-Et-3-Py], [ 2661: 4-Cl-5-Et-3-Py], [2662: 6-Cl-5-Et-3-Py], [2663: 2-Me-5-Et-3-Py], [2664: 4-Me-5-Et-3-Py], [2665: 6-Me-5-Et-3-Py], [2666: 2-CF3-5-Et-3-Py], [2667: 4- CF3-5-Et-3-Py], [2668: 6-CF3-5-Et-3-Py], [2669: 2-CN-5-Et-3-Py], [2670: 4-CN- 5-Et-3-Py], [2671: 6-CN-5-Et-3-Py], [2672: 2-OMe-5-Et-3- y], [2673: 4-OMe-5-Et-3-Py], [2674: 6-OMe-5-Et-3-Py], [2675: 6-Et-3-Py], [2676: 2-Cl-6-Et-3-Py], [2679: 4-Cl-6-Et-3-Py], [2678: 5-Cl-6-Et-3-Py], [2679: 2- Me-6-Et-3-Py], [2680: 4-Me-6-Et-3-Py], [2681: 5-Me-6-Et-3-Py], [2682: 2-CF3- 6-Et-3-Py], [2683: 4-CF3-6-Et-3-Py], [2684: 5-CF3-6-Et-3-Py], [2585: 2-CN-6 Et-3-Py], [2686: 4-CN-6-Et-3-Py], [2687: 5-CN-6-Et-3-Py], [2688: 2-OMe-6-Et-3-Py], [2687: 4-OMe-6-Et-3-Py], [2690: 5-OMe-6-Et-3-Py], [2691 : 2-CH2CF3-3-Py], [2692: 4-Cl-2-CH2CF3-3-Py], [2693: 5-Cl-2-CH2CF3-3-Py], [2694: 6-Cl-2 -CH2CF3-3-Py], [2695: 4-Me-2-CH2CF3-3-Py], [2696: 5-Me-2-CH2CF3-3-Py], [2697: 6-Me-2-CH2CF3 -3-Py], [2698: 4-CF3-2-CH2CF3-3-Py], [2699: 5-CF3-2-CH2CF3-3-Py], [2700: 6-CF3-2-CH2CF3-3 -Py],
[2701:4−CN−2−CH2CF3−3−Py]、[2702:5−CN−2−CH2CF3−3−Py]、[2703:6−CN−2−CH2CF3−3−Py]、[2704:4−OMe−2−CH2CF3−3−Py]、[2705:5−OMe−2−CH2CF3−3−Py]、[2706:6−OMe−2−CH2CF3−3−Py]、[2707:4−CH2CF3−3−Py]、[2708:2−Cl−4−CH2CF3−3−Py]、[2709:5−Cl−4−CH2CF3−3−Py]、[2710:6−Cl−4−CH2CF3−3−Py]、[2711:2−Me−4−CH2CF3−3−Py]、[2712:5−Me−4−CH2CF3−3−Py]、[2713:6−Me−4−CH2CF3−3−Py]、[2714:2−CF3−4−CH2CF3−3−Py]、[2715:5−CF3−4−CH2CF3−3−Py]、[2716:6−CF3−4−CH2CF3−3−Py]、[2717:2−CN−4−CH2CF3−3−Py]、[2718:5−CN−4−CH2CF3−3−Py]、[2719:6−CN−4−CH2CF3−3−Py]、[2720:2−OMe−4−CH2CF3−3−Py]、[2721:5−OMe−4−CH2CF3−3−Py]、[2722:6−OMe−4−CH2CF3−3−Py]、[2723:5−CH2CF3−3−Py]、[2724:2−Cl−5−CH2CF3−3−Py]、[2725:4−Cl−5−CH2CF3−3−Py]、[2726:6−Cl−5−CH2CF3−3−Py]、[2727:2−Me−5−CH2CF3−3−Py]、[2728:4−Me−5−CH2CF3−3−Py]、[2729:6−Me−5−CH2CF3−3−Py]、[2730:2−CF3−5−CH2CF3−3−Py]、[2731:4−CF3−5−CH2CF3−3−Py]、[2732:6−CF3−5−CH2CF3−3−Py]、[2733:2−CN−5−CH2CF3−3−Py]、[2734:4−CN−5−CH2CF3−3−Py]、[2735:6−CN−5−CH2CF3−3−Py]、[2736:2−OMe−5−CH2CF3−3−Py]、[2737:4−OMe−5−CH2CF3−3−Py]、[2738:6−OMe−5−CH2CF3−3−Py]、[2739:6−CH2CF3−3−Py]、[2740:2−Cl−6−CH2CF3−3−Py]、[2741:4−Cl−6−CH2CF3−3−Py]、[2742:5−Cl−6−CH2CF3−3−Py]、[2743:2−Me−6−CH2CF3−3−Py]、[2744:4−Me−6−CH2CF3−3−Py]、[2745:5−Me−6−CH2CF3−3−Py]、[2746:2−CF3−6−CH2CF3−3−Py]、[2747:4−CF3−6−CH2CF3−3−Py]、[2748:5−CF3−6−CH2CF3−3−Py]、[2749:2−CN−6−CH2CF3−3−Py]、[2750:4−CN−6−CH2CF3−3−Py]、[2751:5−CN−6−CH2CF3−3−Py]、[2752:2−OMe−6−CH2CF3−3−Py]、[2753:4−OMe−6−CH2CF3−3−Py]、[2754:5−OMe−6−CH2CF3−3−Py]、[2755:2−OEt−3−Py]、[2756:4−Cl−2−OEt−3−Py]、[2757:5−Cl−2−OEt−3−Py]、[2758:6−Cl−2−OEt−3−Py]、[2759:4−Me−2−OEt−3−Py]、[2760:5−Me−2−OEt−3−Py]、[2761:6−Me−2−OEt−3−Py]、[2762:4−CF3−2−OEt−3−Py]、[2763:5−CF3−2−OEt−3−Py]、[2764:6−CF3−2−OEt−3−Py]、[2765:4−CN−2−OEt−3−Py]、[2766:5−CN−2−OEt−3−Py]、[2767:6−CN−2−OEt−3−Py]、[2768:4−OMe−2−OEt−3−Py]、[2769:5−OMe−2−OEt−3−Py]、[2770:6−OMe−2−OEt−3−Py]、[2771:4−OEt−3−Py]、[2772:2−Cl−4−OEt−3−Py]、[2773:5−Cl−4−OEt−3−Py]、[2774:6−Cl−4−OEt−3−Py]、[2775:2−Me−4−OEt−3−Py]、[2776:5−Me−4−OEt−3−Py]、[2777:6−Me−4−OEt−3−Py]、[2778:2−CF3−4−OEt−3−Py]、[2779:5−CF3−4−OEt−3−Py]、[2780:6−CF3−4−OEt−3−Py]、[2781:2−CN−4−OEt−3−Py]、[2782:5−CN−4−OEt−3−Py]、[2783:6−CN−4−OEt−3−Py]、[2784:2−OMe−4−OEt−3−Py]、[2785:5−OMe−4−OEt−3−Py]、[2786:6−OMe−4−OEt−3−Py]、[2787:5−OEt−3−Py]、[2788:2−Cl−5−OEt−3−Py]、[2789:4−Cl−5−OEt−3−Py]、[2790:6−Cl−5−OEt−3−Py]、[2791:2−Me−5−OEt−3−Py]、[2792:4−Me−5−OEt−3−Py]、[2793:6−Me−5−OEt−3−Py]、[2794:2−CF3−5−OEt−3−Py]、[2795:4−CF3−5−OEt−3−Py]、[2796:6−CF3−5−OEt−3−Py]、[2797:2−CN−5−OEt−3−Py]、[2798:4−CN−5−OEt−3−Py]、[2799:6−CN−5−OEt−3−Py]、[2800:2−OMe−5−OEt−3−Py]、 [2701: 4-CN-2-CH2CF3-3-Py], [2702: 5-CN-2-CH2CF3-3-Py], [2703: 6-CN-2-CH2CF3-3-Py], [2704 : 4-OMe-2-CH2CF3-3-Py], [2705: 5-OMe-2-CH2CF3-3-Py], [2706: 6-OMe-2-CH2CF3-3-Py], [2707: 4 -CH2CF3-3-Py], [2708: 2-Cl-4-CH2CF3-3-Py], [2709: 5-Cl-4-CH2CF3-3-Py], [2710: 6-Cl-4-CH2CF3 -3-Py], [2711: 2-Me-4-CH2CF3-3-Py], [2712: 5-Me-4-CH2CF3-3-Py], [2713: 6-Me-4-CH2CF3-3 -P ], [2714: 2-CF3-4-CH2CF3-3-Py], [2715: 5-CF3-4-CH2CF3-3-Py], [2716: 6-CF3-4-CH2CF3-3-Py], [2717: 2-CN-4-CH2CF3-3-Py], [2718: 5-CN-4-CH2CF3-3-Py], [2719: 6-CN-4-CH2CF3-3-Py], [2720 : 2-OMe-4-CH2CF3-3-Py], [2721: 5-OMe-4-CH2CF3-3-Py], [2722: 6-OMe-4-CH2CF3-3-Py], [2723: 5] -CH2CF3-3-Py], [2724: 2-Cl-5-CH2CF3-3-Py], [2725: 4-Cl-5-CH2CF3-3-Py], [2726: 6-Cl-5-CH2C 3-3-Py], [2727: 2-Me-5-CH2CF3-3-Py], [2728: 4-Me-5-CH2CF3-3-Py], [2729: 6-Me-5-CH2CF3- 3-Py], [2730: 2-CF3-5-CH2CF3-3-Py], [2731: 4-CF3-5-CH2CF3-3-Py], [2732: 6-CF3-5-CH2CF3-3- Py], [2733: 2-CN-5-CH2CF3-3-Py], [2734: 4-CN-5-CH2CF3-3-Py], [2735: 6-CN-5-CH2CF3-3-Py] [2736: 2-OMe-5-CH2CF3-3-Py], [2737: 4-OMe-5-CH2CF3-3-Py], [2738: 6-OMe-5-CH2CF3-3-Py], [ 2739: 6 -CH2CF3-3-Py], [2740: 2-Cl-6-CH2CF3-3-Py], [2741: 4-Cl-6-CH2CF3-3-Py], [2742: 5-Cl-6-CH2CF3 -3-Py], [2743: 2-Me-6-CH2CF3-3-Py], [2744: 4-Me-6-CH2CF3-3-Py], [2745: 5-Me-6-CH2CF3-3. -Py], [2746: 2-CF3-6-CH2CF3-3-Py], [2747: 4-CF3-6-CH2CF3-3-Py], [2748: 5-CF3-6-CH2CF3-3-Py ], [2749: 2-CN-6-CH2CF3-3-Py], [2750: 4-CN-6-CH2CF3-3-Py], [2751: 5-CN-6-CH2CF3-3-Py], [275 : 2-OMe-6-CH2CF3-3-Py], [2753: 4-OMe-6-CH2CF3-3-Py], [2754: 5-OMe-6-CH2CF3-3-Py], [2755: 2] -OEt-3-Py], [2756: 4-Cl-2-OEt-3-Py], [2757: 5-Cl-2-OEt-3-Py], [2758: 6-Cl-2-OEt -3-Py], [2759: 4-Me-2-OEt-3-Py], [2760: 5-Me-2-OEt-3-Py], [2761: 6-Me-2-OEt-3 -Py], [2762: 4-CF3-2-OEt-3-Py], [2763: 5-CF3-2-OEt-3-Py], [2764: 6-CF3-2-OEt-3-Py] ], [2765: 4-CN-2-OEt-3-Py], [2766 5-CN-2-OEt-3-Py], [2767: 6-CN-2-OEt-3-Py], [2768: 4-OMe-2-OEt-3-Py], [2769: 5- OMe-2-OEt-3-Py], [2770: 6-OMe-2-OEt-3-Py], [2771: 4-OEt-3-Py], [2772: 2-Cl-4-OEt- 3-Py], [2773: 5-Cl-4-OEt-3-Py], [2774: 6-Cl-4-OEt-3-Py], [2775: 2-Me-4-OEt-3- Py], [2776: 5-Me-4-OEt-3-Py], [2777: 6-Me-4-OEt-3-Py], [2778: 2-CF3-4-OEt-3-Py] [2779: 5-CF3-4-OEt-3-Py], [2780: 6-CF3-4-OEt -3-Py], [2781: 2-CN-4-OEt-3-Py], [2782: 5-CN-4-OEt-3-Py], [2783: 6-CN-4-OEt-3 -Py], [2784: 2-OMe-4-OEt-3-Py], [2785: 5-OMe-4-OEt-3-Py], [2786: 6-OMe-4-OEt-3-Py ], [2787: 5-OEt-3-Py], [2788: 2-Cl-5-OEt-3-Py], [2789: 4-Cl-5-OEt-3-Py], [2790: 6 -Cl-5-OEt-3-Py], [2791: 2-Me-5-OEt-3-Py], [2792: 4-Me-5-OEt-3-Py], [2793: 6-Me -5-OEt-3-Py], [2794: 2-CF3-5-OEt-3-Py], [2795 4-CF3-5-OEt-3-Py], [2796: 6-CF3-5-OEt-3-Py], [2797: 2-CN-5-OEt-3-Py], [2798: 4- CN-5-OEt-3-Py], [2799: 6-CN-5-OEt-3-Py], [2800: 2-OMe-5-OEt-3-Py],
[2801:4−OMe−5−OEt−3−Py]、[2802:6−OMe−5−OEt−3−Py]、[2803:6−OEt−3−Py]、[2804:2−Cl−6−OEt−3−Py]、[2805:4−Cl−6−OEt−3−Py]、[2806:5−Cl−6−OEt−3−Py]、[2807:2−Me−6−OEt−3−Py]、[2808:4−Me−6−OEt−3−Py]、[2809:5−Me−6−OEt−3−Py]、[2810:2−CF3−6−OEt−3−Py]、[2811:4−CF3−6−OEt−3−Py]、[2812:5−CF3−6−OEt−3−Py]、[2813:2−CN−6−OEt−3−Py]、[2814:4−CN−6−OEt−3−Py]、[2815:5−CN−6−OEt−3−Py]、[2816:2−OMe−6−OEt−3−Py]、[2817:4−OMe−6−OEt−3−Py]、[2818:5−OMe−6−OEt−3−Py]、[2819:2−OCH2CF3−3−Py]、[2820:4−Cl−2−OCH2CF3−3−Py]、[2821:5−Cl−2−OCH2CF3−3−Py]、[2822:6−Cl−2−OCH2CF3−3−Py]、[2823:4−Me−2−OCH2CF3−3−Py]、[2824:5−Me−2−OCH2CF3−3−Py]、[2825:6−Me−2−OCH2CF3−3−Py]、[2826:4−CF3−2−OCH2CF3−3−Py]、[2827:5−CF3−2−OCH2CF3−3−Py]、[2828:6−CF3−2−OCH2CF3−3−Py]、[2829:4−CN−2−OCH2CF3−3−Py]、[2830:5−CN−2−OCH2CF3−3−Py]、[2831:6−CN−2−OCH2CF3−3−Py]、[2832:4−OMe−2−OCH2CF3−3−Py]、[2833:5−OMe−2−OCH2CF3−3−Py]、[2834:6−OMe−2−OCH2CF3−3−Py]、[2835:4−OCH2CF3−3−Py]、[2836:2−Cl−4−OCH2CF3−3−Py]、[2837:5−Cl−4−OCH2CF3−3−Py]、[2838:6−Cl−4−OCH2CF3−3−Py]、[2839:2−Me−4−OCH2CF3−3−Py]、[2840:5−Me−4−OCH2CF3−3−Py]、[2841:6−Me−4−OCH2CF3−3−Py]、[2842:2−CF3−4−OCH2CF3−3−Py]、[2843:5−CF3−4−OCH2CF3−3−Py]、[2844:6−CF3−4−OCH2CF3−3−Py]、[2845:2−CN−4−OCH2CF3−3−Py]、[2846:5−CN−4−OCH2CF3−3−Py]、[2847:6−CN−4−OCH2CF3−3−Py]、[2848:2−OMe−4−OCH2CF3−3−Py]、[2849:5−OMe−4−OCH2CF3−3−Py]、[2850:6−OMe−4−OCH2CF3−3−Py]、[2851:5−OCH2CF3−3−Py]、[2852:2−Cl−5−OCH2CF3−3−Py]、[2853:4−Cl−5−OCH2CF3−3−Py]、[2854:6−Cl−5−OCH2CF3−3−Py]、[2855:2−Me−5−OCH2CF3−3−Py]、[2856:4−Me−5−OCH2CF3−3−Py]、[2857:6−Me−5−OCH2CF3−3−Py]、[2858:2−CF3−5−OCH2CF3−3−Py]、[2859:4−CF3−5−OCH2CF3−3−Py]、[2860:6−CF3−5−OCH2CF3−3−Py]、[2861:2−CN−5−OCH2CF3−3−Py]、[2862:4−CN−5−OCH2CF3−3−Py]、[2863:6−CN−5−OCH2CF3−3−Py]、[2864:2−OMe−5−OCH2CF3−3−Py]、[2865:4−OMe−5−OCH2CF3−3−Py]、[2866:6−OMe−5−OCH2CF3−3−Py]、[2867:6−OCH2CF3−3−Py]、[2868:2−Cl−6−OCH2CF3−3−Py]、[2869:4−Cl−6−OCH2CF3−3−Py]、[2870:5−Cl−6−OCH2CF3−3−Py]、[2871:2−Me−6−OCH2CF3−3−Py]、[2872:4−Me−6−OCH2CF3−3−Py]、[2873:5−Me−6−OCH2CF3−3−Py]、[2874:2−CF3−6−OCH2CF3−3−Py]、[2875:4−CF3−6−OCH2CF3−3−Py]、[2876:5−CF3−6−OCH2CF3−3−Py]、[2877:2−CN−6−OCH2CF3−3−Py]、[2878:4−CN−6−OCH2CF3−3−Py]、[2879:5−CN−6−OCH2CF3−3−Py]、[2880:2−OMe−6−OCH2CF3−3−Py]、[2881:4−OMe−6−OCH2CF3−3−Py]、[2882:5−OMe−6−OCH2CF3−3−Py]、[2883:2−Pr−3−Py]、[2884:4−Cl−2−Pr−3−Py]、[2885:5−Cl−2−Pr−3−Py]、[2886:6−Cl−2−Pr−3−Py]、[2887:4−Me−2−Pr−3−Py]、[2888:5−Me−2−Pr−3−Py]、[2889:6−Me−2−Pr−3−Py]、[2890:4−CF3−2−Pr−3−Py]、[2891:5−CF3−2−Pr−3−Py]、[2892:6−CF3−2−Pr−3−Py]、[2893:4−CN−2−Pr−3−Py]、[2894:5−CN−2−Pr−3−Py]、[2895:6−CN−2−Pr−3−Py]、[2896:4−OMe−2−Pr−3−Py]、[2897:5−OMe−2−Pr−3−Py]、[2898:6−OMe−2−Pr−3−Py]、[2899:4−Pr−3−Py]、[2900:2−Cl−4−Pr−3−Py]、 [2801: 4-OMe-5-OEt-3-Py], [2802: 6-OMe-5-OEt-3-Py], [2803: 6-OEt-3-Py], [2804: 2-Cl -6-OEt-3-Py], [2805: 4-Cl-6-OEt-3-Py], [2806: 5-Cl-6-OEt-3-Py], [2807: 2-Me-6 -OEt-3-Py], [2808: 4-Me-6-OEt-3-Py], [2809: 5-Me-6-OEt-3-Py], [2810: 2-CF3-6-OEt -3-Py], [2811: 4-CF3-6-OEt-3-Py], [2812: 5-CF3-6-OEt-3-Py], [2813: 2-CN-6-OEt-3 -Py], [2814: 4-CN-6-OEt-3-Py], [2815: 5-CN- -OEt-3-Py], [2816: 2-OMe-6-OEt-3-Py], [2817: 4-OMe-6-OEt-3-Py], [2818: 5-OMe-6-OEt -3-Py], [2819: 2-OCH2CF3-3-Py], [2820: 4-Cl-2-OCH2CF3-3-Py], [2821: 5-Cl-2-OCH2CF3-3-Py], [2822: 6-Cl-2-OCH2CF3-3-Py], [2823: 4-Me-2-OCH2CF3-3-Py], [2824: 5-Me-2-OCH2CF3-3-Py], [2825 : 6-Me-2-OCH2CF3-3-Py], [2826: 4-CF3-2-OCH2CF3-3-Py], [2827: 5-CF3-2-OCH2CF3-3-Py], [2828: 6 -C 3-2-OCH2CF3-3-Py], [2829: 4-CN-2-OCH2CF3-3-Py], [2830: 5-CN-2-OCH2CF3-3-Py], [2831: 6-CN- 2-OCH2CF3-3-Py], [2832: 4-OMe-2-OCH2CF3-3-Py], [2833: 5-OMe-2-OCH2CF3-3-Py], [2834: 6-OMe-2- OCH2CF3-3-Py], [2835: 4-OCH2CF3-3-Py], [2836: 2-Cl-4-OCH2CF3-3-Py], [2837: 5-Cl-4-OCH2CF3-3-Py] [2838: 6-Cl-4-OCH2CF3-3-Py], [2839: 2-Me-4-OCH2CF3-3-Py], [2840: 5-Me-4-OCH2CF3 -3-Py], [2841: 6-Me-4-OCH2CF3-3-Py], [2842: 2-CF3-4-OCH2CF3-3-Py], [2843: 5-CF3-4-OCH2CF3-3. -Py], [2844: 6-CF3-4-OCH2CF3-3-Py], [2845: 2-CN-4-OCH2CF3-3-Py], [2846: 5-CN-4-OCH2CF3-3-Py] ], [2847: 6-CN-4-OCH2CF3-3-Py], [2848: 2-OMe-4-OCH2CF3-3-Py], [2849: 5-OMe-4-OCH2CF3-3-Py], [2850: 6-OMe-4-OCH2CF3-3-Py], [2851: 5-OCH2CF3-3-Py], [2852: 2-Cl-5-OCH2CF3-3-Py], [ 853: 4-Cl-5-OCH2CF3-3-Py], [2854: 6-Cl-5-OCH2CF3-3-Py], [2855: 2-Me-5-OCH2CF3-3-Py], [2856: 4-Me-5-OCH2CF3-3-Py], [2857: 6-Me-5-OCH2CF3-3-Py], [2858: 2-CF3-5-OCH2CF3-3-Py], [2859: 4- CF3-5-OCH2CF3-3-Py], [2860: 6-CF3-5-OCH2CF3-3-Py], [2861: 2-CN-5-OCH2CF3-3-Py], [2862: 4-CN- 5-OCH2CF3-3-Py], [2863: 6-CN-5-OCH2CF3-3-Py], [2864: 2-OMe-5-OCH2CF3-3-Py], [2865: -OMe-5-OCH2CF3-3-Py], [2866: 6-OMe-5-OCH2CF3-3-Py], [2867: 6-OCH2CF3-3-Py], [2868: 2-Cl-6-OCH2CF3 -3-Py], [2869: 4-Cl-6-OCH2CF3-3-Py], [2870: 5-Cl-6-OCH2CF3-3-Py], [2871: 2-Me-6-OCH2CF3-3. -Py], [2872: 4-Me-6-OCH2CF3-3-Py], [2873: 5-Me-6-OCH2CF3-3-Py], [2874: 2-CF3-6-OCH2CF3-3-Py]. ], [2875: 4-CF3-6-OCH2CF3-3-Py], [2876: 5-CF3-6-OCH2CF3-3-Py], [2877: 2-CN-6-OCH. 2CF3-3-Py], [2878: 4-CN-6-OCH2CF3-3-Py], [2879: 5-CN-6-OCH2CF3-3-Py], [2880: 2-OMe-6-OCH2CF3- 3-Py], [2881: 4-OMe-6-OCH2CF3-3-Py], [2882: 5-OMe-6-OCH2CF3-3-Py], [2883: 2-Pr-3-Py], [ 2884: 4-Cl-2-Pr-3-Py], [2885: 5-Cl-2-Pr-3-Py], [2886: 6-Cl-2-Pr-3-Py], [2887: 4-Me-2-Pr-3-Py], [2888: 5-Me-2-Pr-3-Py], [2889: 6-Me-2-Pr-3-Py], [2890: 4- CF3-2-Pr-3-Py], [2891: 5-CF3- -Pr-3-Py], [2892: 6-CF3-2-Pr-3-Py], [2893: 4-CN-2-Pr-3-Py], [2894: 5-CN-2-Pr -3-Py], [2895: 6-CN-2-Pr-3-Py], [2896: 4-OMe-2-Pr-3-Py], [2897: 5-OMe-2-Pr-3 -Py], [2898: 6-OMe-2-Pr-3-Py], [2899: 4-Pr-3-Py], [2900: 2-Cl-4-Pr-3-Py],
[2901:5−Cl−4−Pr−3−Py]、[2902:6−Cl−4−Pr−3−Py]、[2903:2−Me−4−Pr−3−Py]、[2904:5−Me−4−Pr−3−Py]、[2905:6−Me−4−Pr−3−Py]、[2906:2−CF3−4−Pr−3−Py]、[2907:5−CF3−4−Pr−3−Py]、[2908:6−CF3−4−Pr−3−Py]、[2909:2−CN−4−Pr−3−Py]、[2910:5−CN−4−Pr−3−Py]、[2911:6−CN−4−Pr−3−Py]、[2912:2−OMe−4−Pr−3−Py]、[2913:5−OMe−4−Pr−3−Py]、[2914:6−OMe−4−Pr−3−Py]、[2915:5−Pr−3−Py]、[2916:2−Cl−5−Pr−3−Py]、[2917:4−Cl−5−Pr−3−Py]、[2918:6−Cl−5−Pr−3−Py]、[2919:2−Me−5−Pr−3−Py]、[2920:4−Me−5−Pr−3−Py]、[2921:6−Me−5−Pr−3−Py]、[2922:2−CF3−5−Pr−3−Py]、[2923:4−CF3−5−Pr−3−Py]、[2924:6−CF3−5−Pr−3−Py]、[2925:2−CN−5−Pr−3−Py]、[2926:4−CN−5−Pr−3−Py]、[2927:6−CN−5−Pr−3−Py]、[2928:2−OMe−5−Pr−3−Py]、[2929:4−OMe−5−Pr−3−Py]、[2930:6−OMe−5−Pr−3−Py]、[2931:6−Pr−3−Py]、[2932:2−Cl−6−Pr−3−Py]、[2933:4−Cl−6−Pr−3−Py]、[2934:5−Cl−6−Pr−3−Py]、[2935:2−Me−6−Pr−3−Py]、[2936:4−Me−6−Pr−3−Py]、[2937:5−Me−6−Pr−3−Py]、[2938:2−CF3−6−Pr−3−Py]、[2939:4−CF3−6−Pr−3−Py]、[2940:5−CF3−6−Pr−3−Py]、[2941:2−CN−6−Pr−3−Py]、[2942:4−CN−6−Pr−3−Py]、[2943:5−CN−6−Pr−3−Py]、[2944:2−OMe−6−Pr−3−Py]、[2945:4−OMe−6−Pr−3−Py]、[2946:5−OMe−6−Pr−3−Py]、[2947:2−OPr−3−Py]、[2948:4−Cl−2−OPr−3−Py]、[2949:5−Cl−2−OPr−3−Py]、[2950:6−Cl−2−OPr−3−Py]、[2951:4−Me−2−OPr−3−Py]、[2952:5−Me−2−OPr−3−Py]、[2953:6−Me−2−OPr−3−Py]、[2954:4−CF3−2−OPr−3−Py]、[2955:5−CF3−2−OPr−3−Py]、[2956:6−CF3−2−OPr−3−Py]、[2957:4−CN−2−OPr−3−Py]、[2958:5−CN−2−OPr−3−Py]、[2959:6−CN−2−OPr−3−Py]、[2960:4−OMe−2−OPr−3−Py]、[2961:5−OMe−2−OPr−3−Py]、[2962:6−OMe−2−OPr−3−Py]、[2963:4−OPr−3−Py]、[2964:2−Cl−4−OPr−3−Py]、[2965:5−Cl−4−OPr−3−Py]、[2966:6−Cl−4−OPr−3−Py]、[2967:2−Me−4−OPr−3−Py]、[2968:5−Me−4−OPr−3−Py]、[2969:6−Me−4−OPr−3−Py]、[2970:2−CF3−4−OPr−3−Py]、[2971:5−CF3−4−OPr−3−Py]、[2972:6−CF3−4−OPr−3−Py]、[2973:2−CN−4−OPr−3−Py]、[2974:5−CN−4−OPr−3−Py]、[2975:6−CN−4−OPr−3−Py]、[2976:2−OMe−4−OPr−3−Py]、[2977:5−OMe−4−OPr−3−Py]、[2978:6−OMe−4−OPr−3−Py]、[2979:5−OPr−3−Py]、[2980:2−Cl−5−OPr−3−Py]、[2981:4−Cl−5−OPr−3−Py]、[2982:6−Cl−5−OPr−3−Py]、[2983:2−Me−5−OPr−3−Py]、[2984:4−Me−5−OPr−3−Py]、[2985:6−Me−5−OPr−3−Py]、[2986:2−CF3−5−OPr−3−Py]、[2987:4−CF3−5−OPr−3−Py]、[2988:6−CF3−5−OPr−3−Py]、[2989:2−CN−5−OPr−3−Py]、[2990:4−CN−5−OPr−3−Py]、[2991:6−CN−5−OPr−3−Py]、[2992:2−OMe−5−OPr−3−Py]、[2993:4−OMe−5−OPr−3−Py]、[2994:6−OMe−5−OPr−3−Py]、[2995:6−OPr−3−Py]、[2996:2−Cl−6−OPr−3−Py]、[2997:4−Cl−6−OPr−3−Py]、[2998:5−Cl−6−OPr−3−Py]、[2999:2−Me−6−OPr−3−Py]、[3000:4−Me−6−OPr−3−Py]、 [2901: 5-Cl-4-Pr-3-Py], [2902: 6-Cl-4-Pr-3-Py], [2903: 2-Me-4-Pr-3-Py], [2904] : 5-Me-4-Pr-3-Py], [2905: 6-Me-4-Pr-3-Py], [2906: 2-CF3-4-Pr-3-Py], [2907: 5 -CF3-4-Pr-3-Py], [2908: 6-CF3-4-Pr-3-Py], [2909: 2-CN-4-Pr-3-Py], [2910: 5-CN -4-Pr-3-Py], [2911: 6-CN-4-Pr-3-Py], [2912: 2-OMe-4-Pr-3-Py], [2913: 5-OMe-4 -Pr-3-Py], [2914: 6-OMe-4-Pr-3-Py], [2915: 5-Pr-3-Py], [2 16: 2-Cl-5-Pr-3-Py], [2917: 4-Cl-5-Pr-3-Py], [2918: 6-Cl-5-Pr-3-Py], [2919: 2-Me-5-Pr-3-Py], [2920: 4-Me-5-Pr-3-Py], [2921: 6-Me-5-Pr-3-Py], [2922: 2- CF3-5-Pr-3-Py], [2923: 4-CF3-5-Pr-3-Py], [2924: 6-CF3-5-Pr-3-Py], [2925: 2-CN- 5-Pr-3-Py], [2926: 4-CN-5-Pr-3-Py], [2927: 6-CN-5-Pr-3-Py], [2928: 2-OMe-5 Pr-3-Py], [2929: 4-OMe-5-Pr-3-Py], [2930: 6-OMe-5-Pr-3-Py] [2931: 6-Pr-3-Py], [2932: 2-Cl-6-Pr-3-Py], [2933: 4-Cl-6-Pr-3-Py], [2934: 5-Cl -6-Pr-3-Py], [2935: 2-Me-6-Pr-3-Py], [2936: 4-Me-6-Pr-3-Py], [2937: 5-Me-6. -Pr-3-Py], [2938: 2-CF3-6-Pr-3-Py], [2939: 4-CF3-6-Pr-3-Py], [2940: 5-CF3-6-Pr -3-Py], [2941: 2-CN-6-Pr-3-Py], [2942: 4-CN-6-Pr-3-Py], [2943: 5-CN-6-Pr-3 -Py], [2944: 2-OMe-6-Pr-3-Py], [2945: 4-OMe-6-Pr-3-Py], [29 46: 5-OMe-6-Pr-3-Py], [2947: 2-OPr-3-Py], [2948: 4-Cl-2-OPr-3-Py], [2949: 5-Cl- 2-OPr-3-Py], [2950: 6-Cl-2-OPr-3-Py], [2951: 4-Me-2-OPr-3-Py], [2952: 5-Me-2- OPr-3-Py], [2953: 6-Me-2-OPr-3-Py], [2954: 4-CF3-2-OPr-3-Py], [2955: 5-CF3-2-OPr- 3-Py], [2956: 6-CF3-2-OPr-3-Py], [2957: 4-CN-2-OPr-3-Py], [2958: 5-CN-2-OPr-3- Py], [2959: 6-CN-2-OPr-3-Py], [2960: 4-OMe-2-OP -3-Py], [2961: 5-OMe-2-OPr-3-Py], [2962: 6-OMe-2-OPr-3-Py], [2963: 4-OPr-3-Py], [2964: 2-Cl-4-OPr-3-Py], [2965: 5-Cl-4-OPr-3-Py], [2966: 6-Cl-4-OPr-3-Py], [2967 : 2-Me-4-OPr-3-Py], [2968: 5-Me-4-OPr-3-Py], [2969: 6-Me-4-OPr-3-Py], [2970: 2]. -CF3-4-OPr-3-Py], [2971: 5-CF3-4-OPr-3-Py], [2972: 6-CF3-4-OPr-3-Py], [2973: 2-CN -4-OPr-3-Py], [2974: 5-CN-4-OPr-3-Py], [29 5: 6-CN-4-OPr-3-Py], [2976: 2-OMe-4-OPr-3-Py], [2777: 5-OMe-4-OPr-3-Py], [2978: 6-OMe-4-OPr-3-Py], [2979: 5-OPr-3-Py], [2980: 2-Cl-5-OPr-3-Py], [2981: 4-Cl-5 OPr-3-Py], [2982: 6-Cl-5-OPr-3-Py], [2983: 2-Me-5-OPr-3-Py], [2984: 4-Me-5-OPr- 3-Py], [2985: 6-Me-5-OPr-3-Py], [2986: 2-CF3-5-OPr-3-Py], [2987: 4-CF3-5-OPr-3- Py], [2988: 6-CF3-5-OPr-3-Py], [2989: 2-CN-5-O. Pr-3-Py], [2990: 4-CN-5-OPr-3-Py], [2991: 6-CN-5-OPr-3-Py], [2992: 2-OMe-5-OPr- 3-Py], [2993: 4-OMe-5-OPr-3-Py], [2994: 6-OMe-5-OPr-3-Py], [2995: 6-OPr-3-Py], [ 2996: 2-Cl-6-OPr-3-Py], [2997: 4-Cl-6-OPr-3-Py], [2998: 5-Cl-6-OPr-3-Py], [2999: 2-Me-6-OPr-3-Py], [3000: 4-Me-6-OPr-3-Py],
[3001:5−Me−6−OPr−3−Py]、[3002:2−CF3−6−OPr−3−Py]、[3003:4−CF3−6−OPr−3−Py]、[3004:5−CF3−6−OPr−3−Py]、[3005:2−CN−6−OPr−3−Py]、[3006:4−CN−6−OPr−3−Py]、[3007:5−CN−6−OPr−3−Py]、[3008:2−OMe−6−OPr−3−Py]、[3009:4−OMe−6−OPr−3−Py]、[3010:5−OMe−6−OPr−3−Py]、[3011:2−SMe−3−Py]、[3012:4−Cl−2−SMe−3−Py]、[3013:5−Cl−2−SMe−3−Py]、[3014:6−Cl−2−SMe−3−Py]、[3015:4−Me−2−SMe−3−Py]、[3016:5−Me−2−SMe−3−Py]、[3017:6−Me−2−SMe−3−Py]、[3018:4−CF3−2−SMe−3−Py]、[3019:5−CF3−2−SMe−3−Py]、[3020:6−CF3−2−SMe−3−Py]、[3021:4−CN−2−SMe−3−Py]、[3022:5−CN−2−SMe−3−Py]、[3023:6−CN−2−SMe−3−Py]、[3024:4−OMe−2−SMe−3−Py]、[3025:5−OMe−2−SMe−3−Py]、[3026:6−OMe−2−SMe−3−Py]、[3027:4−SMe−3−Py]、[3028:2−Cl−4−SMe−3−Py]、[3029:5−Cl−4−SMe−3−Py]、[3030:6−Cl−4−SMe−3−Py]、[3031:2−Me−4−SMe−3−Py]、[3032:5−Me−4−SMe−3−Py]、[3033:6−Me−4−SMe−3−Py]、[3034:2−CF3−4−SMe−3−Py]、[3035:5−CF3−4−SMe−3−Py]、[3036:6−CF3−4−SMe−3−Py]、[3037:2−CN−4−SMe−3−Py]、[3038:5−CN−4−SMe−3−Py]、[3039:6−CN−4−SMe−3−Py]、[3040:2−OMe−4−SMe−3−Py]、[3041:5−OMe−4−SMe−3−Py]、[3042:6−OMe−4−SMe−3−Py]、[3043:5−SMe−3−Py]、[3044:2−Cl−5−SMe−3−Py]、[3045:4−Cl−5−SMe−3−Py]、[3046:6−Cl−5−SMe−3−Py]、[3047:2−Me−5−SMe−3−Py]、[3048:4−Me−5−SMe−3−Py]、[3049:6−Me−5−SMe−3−Py]、[3050:2−CF3−5−SMe−3−Py]、[3051:4−CF3−5−SMe−3−Py]、[3052:6−CF3−5−SMe−3−Py]、[3053:2−CN−5−SMe−3−Py]、[3054:4−CN−5−SMe−3−Py]、[3055:6−CN−5−SMe−3−Py]、[3056:2−OMe−5−SMe−3−Py]、[3057:4−OMe−5−SMe−3−Py]、[3058:6−OMe−5−SMe−3−Py]、[3059:6−SMe−3−Py]、[3060:2−Cl−6−SMe−3−Py]、[3061:4−Cl−6−SMe−3−Py]、[3062:5−Cl−6−SMe−3−Py]、[3063:2−Me−6−SMe−3−Py]、[3064:4−Me−6−SMe−3−Py]、[3065:5−Me−6−SMe−3−Py]、[3066:2−CF3−6−SMe−3−Py]、[3067:4−CF3−6−SMe−3−Py]、[3068:5−CF3−6−SMe−3−Py]、[3069:2−CN−6−SMe−3−Py]、[3070:4−CN−6−SMe−3−Py]、[3071:5−CN−6−SMe−3−Py]、[3072:2−OMe−6−SMe−3−Py]、[3073:4−OMe−6−SMe−3−Py]、[3074:5−OMe−6−SMe−3−Py]、[3075:2−SCF3−3−Py]、[3076:4−Cl−2−SCF3−3−Py]、[3077:5−Cl−2−SCF3−3−Py]、[3078:6−Cl−2−SCF3−3−Py]、[3079:4−Me−2−SCF3−3−Py]、[3080:5−Me−2−SCF3−3−Py]、[3081:6−Me−2−SCF3−3−Py]、[3082:4−CF3−2−SCF3−3−Py]、[3083:5−CF3−2−SCF3−3−Py]、[3084:6−CF3−2−SCF3−3−Py]、[3085:4−CN−2−SCF3−3−Py]、[3086:5−CN−2−SCF3−3−Py]、[3087:6−CN−2−SCF3−3−Py]、[3088:4−OMe−2−SCF3−3−Py]、[3089:5−OMe−2−SCF3−3−Py]、[3090:6−OMe−2−SCF3−3−Py]、[3091:4−SCF3−3−Py]、[3092:2−Cl−4−SCF3−3−Py]、[3093:5−Cl−4−SCF3−3−Py]、[3094:6−Cl−4−SCF3−3−Py]、[3095:2−Me−4−SCF3−3−Py]、[3096:5−Me−4−SCF3−3−Py]、[3097:6−Me−4−SCF3−3−Py]、[3098:2−CF3−4−SCF3−3−Py]、[3099:5−CF3−4−SCF3−3−Py]、[3100:6−CF3−4−SCF3−3−Py]、 [3001: 5-Me-6-OPr-3-Py], [3002: 2-CF3-6-OPr-3-Py], [3003: 4-CF3-6-OPr-3-Py], [3004 : 5-CF3-6-OPr-3-Py], [3005: 2-CN-6-OPr-3-Py], [3006: 4-CN-6-OPr-3-Py], [3007: 5 -CN-6-OPr-3-Py], [3008: 2-OMe-6-OPr-3-Py], [3009: 4-OMe-6-OPr-3-Py], [3010: 5-OMe -6-OPr-3-Py], [3011: 2-SMe-3-Py], [3012: 4-Cl-2-SMe-3-Py], [3013: 5-Cl-2-SMe-3 -Py], [3014: 6-Cl-2-SMe-3-Py], [3015: 4-Me 2-SMe-3-Py], [3016: 5-Me-2-SMe-3-Py], [3017: 6-Me-2-SMe-3-Py], [3018: 4-CF3-2- SMe-3-Py], [3019: 5-CF3-2-SMe-3-Py], [3020: 6-CF3-2-SMe-3-Py], [3021: 4-CN-2-SMe- 3-Py], [3022: 5-CN-2-SMe-3-Py], [3023: 6-CN-2-SMe-3-Py], [3024: 4-OMe-2-SMe-3- Py], [3025: 5-OMe-2-SMe-3-Py], [3026: 6-OMe-2-SMe-3-Py], [3027: 4-SMe-3-Py], [3028: 2-Cl-4-SMe-3-Py], [3029: 5-Cl-4-SMe-3-P ], [3030: 6-Cl-4-SMe-3-Py], [3031: 2-Me-4-SMe-3-Py], [3032: 5-Me-4-SMe-3-Py], [3033: 6-Me-4-SMe-3-Py], [3034: 2-CF3-4-SMe-3-Py], [3035: 5-CF3-4-SMe-3-Py], [3036 : 6-CF3-4-SMe-3-Py], [3037: 2-CN-4-SMe-3-Py], [3038: 5-CN-4-SMe-3-Py], [3039: 6 -CN-4-SMe-3-Py], [3040: 2-OMe-4-SMe-3-Py], [3041: 5-OMe-4-SMe-3-Py], [3042: 6-OMe -4-SMe-3-Py], [3043: 5-SMe-3-Py], [3044: 2- Cl-5-SMe-3-Py], [3045: 4-Cl-5-SMe-3-Py], [3046: 6-Cl-5-SMe-3-Py], [3047: 2-Me- 5-SMe-3-Py], [3048: 4-Me-5-SMe-3-Py], [3049: 6-Me-5-SMe-3-Py], [3050: 2-CF3-5 SMe-3-Py], [3051: 4-CF3-5-SMe-3-Py], [3052: 6-CF3-5-SMe-3-Py], [3053: 2-CN-5-SMe- 3-Py], [3054: 4-CN-5-SMe-3-Py], [3055: 6-CN-5-SMe-3-Py], [3056: 2-OMe-5-SMe-3- Py], [3057: 4-OMe-5-SMe-3-Py], [3058: 6-OMe-5-5 Me-3-Py], [3059: 6-SMe-3-Py], [3060: 2-Cl-6-SMe-3-Py], [3061: 4-Cl-6-SMe-3-Py] [3062: 5-Cl-6-SMe-3-Py], [3063: 2-Me-6-SMe-3-Py], [3064: 4-Me-6-SMe-3-Py], [ 3065: 5-Me-6-SMe-3-Py], [3066: 2-CF3-6-SMe-3-Py], [3067: 4-CF3-6-SMe-3-Py], [3068: 5-CF3-6-SMe-3-Py], [3069: 2-CN-6-SMe-3-Py], [3070: 4-CN-6-SMe-3-Py], [3071: 5- CN-6-SMe-3-Py], [3072: 2-OMe-6-SMe-3-Py], [3 73: 4-OMe-6-SMe-3-Py], [3074: 5-OMe-6-SMe-3-Py], [3075: 2-SCF3-3-Py], [3076: 4-Cl- 2-SCF3-3-Py], [3077: 5-Cl-2-SCF3-3-Py], [3078: 6-Cl-2-SCF3-3-Py], [3079: 4-Me-2- SCF3-3-Py], [3080: 5-Me-2-SCF3-3-Py], [3081: 6-Me-2-SCF3-3-Py], [3082: 4-CF3-2-SCF3- 3-Py], [3083: 5-CF3-2-SCF3-3-Py], [3084: 6-CF3-2-SCF3-3-Py], [3085: 4-CN-2-SCF3-3 Py], [3086: 5-CN-2-SCF3-3-Py], [3 087: 6-CN-2-SCF3-3-Py], [3088: 4-OMe-2-SCF3-3-Py], [3089: 5-OMe-2-SCF3-3-Py], [3090: 6-OMe-2-SCF3-3-Py], [3091: 4-SCF3-3-Py], [3092: 2-Cl-4-SCF3-3-Py], [3093: 5-Cl-4- SCF3-3-Py], [3094: 6-Cl-4-SCF3-3-Py], [3095: 2-Me-4-SCF3-3-Py], [3096: 5-Me-4-SCF3- 3-Py], [3097: 6-Me-4-SCF3-3-Py], [3098: 2-CF3-4-SCF3-3-Py], [3099: 5-CF3-4-SCF3-3 Py], [3100: 6-CF3-4-SCF3-3-Py ,
[3101:2−CN−4−SCF3−3−Py]、[3102:5−CN−4−SCF3−3−Py]、[3103:6−CN−4−SCF3−3−Py]、[3104:2−OMe−4−SCF3−3−Py]、[3105:5−OMe−4−SCF3−3−Py]、[3106:6−OMe−4−SCF3−3−Py]、[3107:5−SCF3−3−Py]、[3108:2−Cl−5−SCF3−3−Py]、[3109:4−Cl−5−SCF3−3−Py]、[3110:6−Cl−5−SCF3−3−Py]、[3111:2−Me−5−SCF3−3−Py]、[3112:4−Me−5−SCF3−3−Py]、[3113:6−Me−5−SCF3−3−Py]、[3114:2−CF3−5−SCF3−3−Py]、[3115:4−CF3−5−SCF3−3−Py]、[3116:6−CF3−5−SCF3−3−Py]、[3117:2−CN−5−SCF3−3−Py]、[3118:4−CN−5−SCF3−3−Py]、[3119:6−CN−5−SCF3−3−Py]、[3120:2−OMe−5−SCF3−3−Py]、[3121:4−OMe−5−SCF3−3−Py]、[3122:6−OMe−5−SCF3−3−Py]、[3123:6−SCF3−3−Py]、[3124:2−Cl−6−SCF3−3−Py]、[3125:4−Cl−6−SCF3−3−Py]、[3126:6−Cl−6−SCF3−3−Py]、[3127:2−Me−6−SCF3−3−Py]、[3128:4−Me−6−SCF3−3−Py]、[3129:6−Me−6−SCF3−3−Py]、[3130:2−CF3−6−SCF3−3−Py]、[3131:4−CF3−6−SCF3−3−Py]、[3132:6−CF3−6−SCF3−3−Py]、[3133:2−CN−6−SCF3−3−Py]、[3134:4−CN−6−SCF3−3−Py]、[3135:6−CN−6−SCF3−3−Py]、[3136:2−OMe−6−SCF3−3−Py]、[3137:4−OMe−6−SCF3−3−Py]、[3138:6−OMe−6−SCF3−3−Py]、[3139:2−S(O)Me−3−Py]、[3140:4−Cl−2−S(O)Me−3−Py]、[3141:5−Cl−2−S(O)Me−3−Py]、[3142:6−Cl−2−S(O)Me−3−Py]、[3143:4−Me−2−S(O)Me−3−Py]、[3144:5−Me−2−S(O)Me−3−Py]、[3145:6−Me−2−S(O)Me−3−Py]、[3146:4−CF3−2−S(O)Me−3−Py]、[3147:5−CF3−2−S(O)Me−3−Py]、[3148:6−CF3−2−S(O)Me−3−Py]、[3149:4−CN−2−S(O)Me−3−Py]、[3150:5−CN−2−S(O)Me−3−Py]、[3151:6−CN−2−S(O)Me−3−Py]、[3152:4−OMe−2−S(O)Me−3−Py]、[3153:5−OMe−2−S(O)Me−3−Py]、[3154:6−OMe−2−S(O)Me−3−Py]、[3155:4−S(O)Me−3−Py]、[3156:2−Cl−4−S(O)Me−3−Py]、[3157:5−Cl−4−S(O)Me−3−Py]、[3158:6−Cl−4−S(O)Me−3−Py]、[3159:2−Me−4−S(O)Me−3−Py]、[3160:5−Me−4−S(O)Me−3−Py]、[3161:6−Me−4−S(O)Me−3−Py]、[3162:2−CF3−4−S(O)Me−3−Py]、[3163:5−CF3−4−S(O)Me−3−Py]、[3164:6−CF3−4−S(O)Me−3−Py]、[3165:2−CN−4−S(O)Me−3−Py]、[3166:5−CN−4−S(O)Me−3−Py]、[3167:6−CN−4−S(O)Me−3−Py]、[3168:2−OMe−4−S(O)Me−3−Py]、[3169:5−OMe−4−S(O)Me−3−Py]、[3170:6−OMe−4−S(O)Me−3−Py]、[3171:5−S(O)Me−3−Py]、[3172:2−Cl−5−S(O)Me−3−Py]、[3173:4−Cl−5−S(O)Me−3−Py]、[3174:6−Cl−5−S(O)Me−3−Py]、[3175:2−Me−5−S(O)Me−3−Py]、[3176:4−Me−5−S(O)Me−3−Py]、[3177:6−Me−5−S(O)Me−3−Py]、[3178:2−CF3−5−S(O)Me−3−Py]、[3179:4−CF3−5−S(O)Me−3−Py]、[3180:6−CF3−5−S(O)Me−3−Py]、[3181:2−CN−5−S(O)Me−3−Py]、[3182:4−CN−5−S(O)Me−3−Py]、[3183:6−CN−5−S(O)Me−3−Py]、[3184:2−OMe−5−S(O)Me−3−Py]、[3185:4−OMe−5−S(O)Me−3−Py]、[3186:6−OMe−5−S(O)Me−3−Py]、[3187:6−S(O)Me−3−Py]、[3188:2−Cl−6−S(O)Me−3−Py]、[3189:4−Cl−6−S(O)Me−3−Py]、[3190:5−Cl−6−S(O)Me−3−Py]、[3191:2−Me−6−S(O)Me−3−Py]、[3192:4−Me−6−S(O)Me−3−Py]、[3193:5−Me−6−S(O)Me−3−Py]、[3194:2−CF3−6−S(O)Me−3−Py]、[3195:4−CF3−6−S(O)Me−3−Py]、[3196:5−CF3−6−S(O)Me−3−Py]、[3197:2−CN−6−S(O)Me−3−Py]、[3198:4−CN−6−S(O)Me−3−Py]、[3199:5−CN−6−S(O)Me−3−Py]、[3200:2−OMe−6−S(O)Me−3−Py]、 [3101: 2-CN-4-SCF3-3-Py], [3102: 5-CN-4-SCF3-3-Py], [3103: 6-CN-4-SCF3-3-Py], [3104 : 2-OMe-4-SCF3-3-Py], [3105: 5-OMe-4-SCF3-3-Py], [3106: 6-OMe-4-SCF3-3-Py], [3107: 5 -SCF3-3-Py], [3108: 2-Cl-5-SCF3-3-Py], [3109: 4-Cl-5-SCF3-3-Py], [3110: 6-Cl-5-SCF3 -3-Py], [3111: 2-Me-5-SCF3-3-Py], [3112: 4-Me-5-SCF3-3-Py], [3113: 6-Me-5-SCF3-3 -Py], [3114: 2-CF3-5-SCF3-3-Py [3115: 4-CF3-5-SCF3-3-Py], [3116: 6-CF3-5-SCF3-3-Py], [3117: 2-CN-5-SCF3-3-Py], [ 3118: 4-CN-5-SCF3-3-Py], [3119: 6-CN-5-SCF3-3-Py], [3120: 2-OMe-5-SCF3-3-Py], [3121: 4-OMe-5-SCF3-3-Py], [3122: 6-OMe-5-SCF3-3-Py], [3123: 6-SCF3-3-Py], [3124: 2-Cl-6 SCF3-3-Py], [3125: 4-Cl-6-SCF3-3-Py], [3126: 6-Cl-6-SCF3-3-Py], [3127: 2-Me-6-SCF3- 3-Py], [3128: 4-Me-6-SCF3-3 Py], [3129: 6-Me-6-SCF3-3-Py], [3130: 2-CF3-6-SCF3-3-Py], [3131: 4-CF3-6-SCF3-3-Py] [3132: 6-CF3-6-SCF3-3-Py], [3133: 2-CN-6-SCF3-3-Py], [3134: 4-CN-6-SCF3-3-Py], [ 3135: 6-CN-6-SCF3-3-Py], [3136: 2-OMe-6-SCF3-3-Py], [3137: 4-OMe-6-SCF3-3-Py], [3138: 6-OMe-6-SCF3-3-Py], [3139: 2-S (O) Me-3-Py], [3140: 4-Cl-2-S (O) Me-3-Py], [ 3141: 5-Cl-2-S (O) Me-3-Py], [3142: 6-Cl -2 -S (O) Me-3-Py], [3143: 4-Me-2-S (O) Me-3-Py], [3144: 5-Me-2-S (O) Me-3 -Py], [3145: 6-Me-2-S (O) Me-3-Py], [3146: 4-CF3-2-S (O) Me-3-Py], [3147: 5-CF3. -2-S (O) Me-3-Py], [3148: 6-CF3-2-S (O) Me-3-Py], [3149: 4-CN-2-S (O) Me-3 -Py], [3150: 5-CN-2-S (O) Me-3-Py], [3151: 6-CN-2-S (O) Me-3-Py], [3152: 4-OMe. -2-S (O) Me-3-Py], [3153: 5-OMe-2-S (O) Me-3-Py], [3154: 6-OMe-2-S (O) Me-3 -Py] [3155: 4-S (O) Me-3-Py], [3156: 2-Cl-4-S (O) Me-3-Py], [3157: 5-Cl-4-S (O) Me -3-Py], [3158: 6-Cl-4-S (O) Me-3-Py], [3159: 2-Me-4-S (O) Me-3-Py], [3160: 5 -Me-4-S (O) Me-3-Py], [3161: 6-Me-4-S (O) Me-3-Py], [3162: 2-CF3-4-S (O) Me -3-Py], [3163: 5-CF3-4-S (O) Me-3-Py], [3164: 6-CF3-4-S (O) Me-3-Py], [3165: 2 -CN-4-S (O) Me-3-Py], [3166: 5-CN-4-S (O) Me-3-Py], [3167: 6-CN-4-S (O) Me -3- y], [3168: 2-OMe-4-S (O) Me-3-Py], [3169: 5-OMe-4-S (O) Me-3-Py], [3170: 6-OMe- 4-S (O) Me-3-Py], [3171: 5-S (O) Me-3-Py], [3172: 2-Cl-5-S (O) Me-3-Py], [ 3173: 4-Cl-5-S (O) Me-3-Py], [3174: 6-Cl-5-S (O) Me-3-Py], [3175: 2-Me-5-S ( O) Me-3-Py], [3176: 4-Me-5-S (O) Me-3-Py], [3177: 6-Me-5-S (O) Me-3-Py], [ 3178: 2-CF3-5-S (O) Me-3-Py], [3179: 4-CF3-5-S (O) Me-3-Py], [3180: 6-CF3-5-S ( O) Me-3-Py], [3181: 2-CN-5-S (O) Me-3-Py], [3182: 4-CN-5-S (O) Me-3-Py], [3183: 6-CN-5-S (O) Me-3-Py], [3184: 2-OMe-5-S (O) Me-3-Py], [3185: 4-OMe-5-S (O) Me-3-Py], [3186: 6-OMe-5-S (O) Me-3-Py], [3187: 6-S (O) Me-3-Py], [3188: 2-Cl- 6-S (O) Me-3-Py], [3189: 4-Cl-6-S (O) Me-3-Py], [3190: 5-Cl-6-S (O) Me-3- Py], [3191: 2-Me-6-S (O) Me-3-Py], [3192: 4-Me-6-S (O) Me-3-Py], [3193: 5-Me- 6-S O) Me-3-Py], [3194: 2-CF3-6-S (O) Me-3-Py], [3195: 4-CF3-6-S (O) Me-3-Py], [ 3196: 5-CF3-6-S (O) Me-3-Py], [3197: 2-CN-6-S (O) Me-3-Py], [3198: 4-CN-6-S ( O) Me-3-Py], [3199: 5-CN-6-S (O) Me-3-Py], [3200: 2-OMe-6-S (O) Me-3-Py],
[3201:4−OMe−6−S(O)Me−3−Py]、[3202:5−OMe−6−S(O)Me−3−Py]、[3203:2−S(O)CF3−3−Py]、[3204:4−Cl−2−S(O)CF3−3−Py]、[3205:5−Cl−2−S(O)CF3−3−Py]、[3206:6−Cl−2−S(O)CF3−3−Py]、[3207:4−Me−2−S(O)CF3−3−Py]、[3208:5−Me−2−S(O)CF3−3−Py]、[3209:6−Me−2−S(O)CF3−3−Py]、[3210:4−CF3−2−S(O)CF3−3−Py]、[3211:5−CF3−2−S(O)CF3−3−Py]、[3212:6−CF3−2−S(O)CF3−3−Py]、[3213:4−CN−2−S(O)CF3−3−Py]、[3214:5−CN−2−S(O)CF3−3−Py]、[3215:6−CN−2−S(O)CF3−3−Py]、[3216:4−OMe−2−S(O)CF3−3−Py]、[3217:5−OMe−2−S(O)CF3−3−Py]、[3218:6−OMe−2−S(O)CF3−3−Py]、[3219:4−S(O)CF3−3−Py]、[3220:2−Cl−4−S(O)CF3−3−Py]、[3221:5−Cl−4−S(O)CF3−3−Py]、[3222:6−Cl−4−S(O)CF3−3−Py]、[3223:2−Me−4−S(O)CF3−3−Py]、[3224:5−Me−4−S(O)CF3−3−Py]、[3225:6−Me−4−S(O)CF3−3−Py]、[3226:2−CF3−4−S(O)CF3−3−Py]、[3227:5−CF3−4−S(O)CF3−3−Py]、[3228:6−CF3−4−S(O)CF3−3−Py]、[3229:2−CN−4−S(O)CF3−3−Py]、[3230:5−CN−4−S(O)CF3−3−Py]、[3231:6−CN−4−S(O)CF3−3−Py]、[3232:2−OMe−4−S(O)CF3−3−Py]、[3233:5−OMe−4−S(O)CF3−3−Py]、[3234:6−OMe−4−S(O)CF3−3−Py]、[3235:5−S(O)CF3−3−Py]、[3236:2−Cl−5−S(O)CF3−3−Py]、[3237:4−Cl−5−S(O)CF3−3−Py]、[3238:6−Cl−5−S(O)CF3−3−Py]、[3239:2−Me−5−S(O)CF3−3−Py]、[3240:4−Me−5−S(O)CF3−3−Py]、[3241:6−Me−5−S(O)CF3−3−Py]、[3242:2−CF3−5−S(O)CF3−3−Py]、[3243:4−CF3−5−S(O)CF3−3−Py]、[3244:6−CF3−5−S(O)CF3−3−Py]、[3245:2−CN−5−S(O)CF3−3−Py]、[3246:4−CN−5−S(O)CF3−3−Py]、[3247:6−CN−5−S(O)CF3−3−Py]、[3248:2−OMe−5−S(O)CF3−3−Py]、[3249:4−OMe−5−S(O)CF3−3−Py]、[3250:6−OMe−5−S(O)CF3−3−Py]、[3251:6−S(O)CF3−3−Py]、[3252:2−Cl−6−S(O)CF3−3−Py]、[3253:4−Cl−6−S(O)CF3−3−Py]、[3254:5−Cl−6−S(O)CF3−3−Py]、[3255:2−Me−6−S(O)CF3−3−Py]、[3256:4−Me−6−S(O)CF3−3−Py]、[3257:5−Me−6−S(O)CF3−3−Py]、[3258:2−CF3−6−S(O)CF3−3−Py]、[3259:4−CF3−6−S(O)CF3−3−Py]、[3260:5−CF3−6−S(O)CF3−3−Py]、[3261:2−CN−6−S(O)CF3−3−Py]、[3262:4−CN−6−S(O)CF3−3−Py]、[3263:5−CN−6−S(O)CF3−3−Py]、[3264:2−OMe−6−S(O)CF3−3−Py]、[3265:4−OMe−6−S(O)CF3−3−Py]、[3266:5−OMe−6−S(O)CF3−3−Py]、[3267:2−S(O)2Me−3−Py]、[3268:4−Cl−2−S(O)2Me−3−Py]、[3269:5−Cl−2−S(O)2Me−3−Py]、[3270:6−Cl−2−S(O)2Me−3−Py]、[3271:4−Me−2−S(O)2Me−3−Py]、[3272:5−Me−2−S(O)2Me−3−Py]、[3273:6−Me−2−S(O)2Me−3−Py]、[3274:4−CF3−2−S(O)2Me−3−Py]、[3275:5−CF3−2−S(O)2Me−3−Py]、[3276:6−CF3−2−S(O)2Me−3−Py]、[3277:4−CN−2−S(O)2Me−3−Py]、[3278:5−CN−2−S(O)2Me−3−Py]、[3279:6−CN−2−S(O)2Me−3−Py]、[3280:4−OMe−2−S(O)2Me−3−Py]、[3281:5−OMe−2−S(O)2Me−3−Py]、[3282:6−OMe−2−S(O)2Me−3−Py]、[3283:4−S(O)2Me−3−Py]、[3284:2−Cl−4−S(O)2Me−3−Py]、[3285:5−Cl−4−S(O)2Me−3−Py]、[3286:6−Cl−4−S(O)2Me−3−Py]、[3287:2−Me−4−S(O)2Me−3−Py]、[3288:5−Me−4−S(O)2Me−3−Py]、[3289:6−Me−4−S(O)2Me−3−Py]、[3290:2−CF3−4−S(O)2Me−3−Py]、[3291:5−CF3−4−S(O)2Me−3−Py]、[3292:6−CF3−4−S(O)2Me−3−Py]、[3293:2−CN−4−S(O)2Me−3−Py]、[3294:5−CN−4−S(O)2Me−3−Py]、[3295:6−CN−4−S(O)2Me−3−Py]、[3296:2−OMe−4−S(O)2Me−3−Py]、[3297:5−OMe−4−S(O)2Me−3−Py]、[3298:6−OMe−4−S(O)2Me−3−Py]、[3299:5−S(O)2Me−3−Py]、[3300:2−Cl−5−S(O)2Me−3−Py]、 [3201: 4-OMe-6-S (O) Me-3-Py], [3202: 5-OMe-6-S (O) Me-3-Py], [3203: 2-S (O) CF3 -3-Py], [3204: 4-Cl-2-S (O) CF3-3-Py], [3205: 5-Cl-2-S (O) CF3-3-Py], [3206: 6 -Cl-2-S (O) CF3-3-Py], [3207: 4-Me-2-S (O) CF3-3-Py], [3208: 5-Me-2-S (O) CF3 -3-Py], [3209: 6-Me-2-S (O) CF3-3-Py], [3210: 4-CF3-2-S (O) CF3-3-Py], [3211: 5 -CF3-2-S (O) CF3-3-Py], [3212: 6-CF3-2-S (O) CF3-3-Py], [3213: 4-CN- -S (O) CF3-3-Py], [3214: 5-CN-2-S (O) CF3-3-Py], [3215: 6-CN-2-S (O) CF3-3-Py ], [3216: 4-OMe-2-S (O) CF3-3-Py], [3217: 5-OMe-2-S (O) CF3-3-Py], [3218: 6-OMe-2 -S (O) CF3-3-Py], [3219: 4-S (O) CF3-3-Py], [3220: 2-Cl-4-S (O) CF3-3-Py], [3221 : 5-Cl-4-S (O) CF3-3-Py], [3222: 6-Cl-4-S (O) CF3-3-Py], [3223: 2-Me-4-S (O ) CF3-3-Py], [3224: 5-Me-4-S (O) CF3-3-Py], [3225: 6-Me-4-S (O) CF3-3. Py], [3226: 2-CF3-4-S (O) CF3-3-Py], [3227: 5-CF3-4-S (O) CF3-3-Py], [3228: 6-CF3- 4-S (O) CF3-3-Py], [3229: 2-CN-4-S (O) CF3-3-Py], [3230: 5-CN-4-S (O) CF3-3- Py], [3231: 6-CN-4-S (O) CF3-3-Py], [3232: 2-OMe-4-S (O) CF3-3-Py], [3233: 5-OMe- 4-S (O) CF3-3-Py], [3234: 6-OMe-4-S (O) CF3-3-Py], [3235: 5-S (O) CF3-3-Py], [ 3236: 2-Cl-5-S (O) CF3-3-Py], [3237: 4-Cl-5-S (O) CF3-3-Py], [323 8: 6-Cl-5-S (O) CF3-3-Py], [3239: 2-Me-5-S (O) CF3-3-Py], [3240: 4-Me-5-S ( O) CF3-3-Py], [3241: 6-Me-5-S (O) CF3-3-Py], [3242: 2-CF3-5-S (O) CF3-3-Py], [ 3243: 4-CF3-5-S (O) CF3-3-Py], [3244: 6-CF3-5-S (O) CF3-3-Py], [3245: 2-CN-5-S ( O) CF3-3-Py], [3246: 4-CN-5-S (O) CF3-3-Py], [3247: 6-CN-5-S (O) CF3-3-Py], [ 3248: 2-OMe-5-S (O) CF3-3-Py], [3249: 4-OMe-5-S (O) CF3-3-Py], [3250: 6- Me-5-S (O) CF3-3-Py], [3251: 6-S (O) CF3-3-Py], [3252: 2-Cl-6-S (O) CF3-3-Py] [3253: 4-Cl-6-S (O) CF3-3-Py], [3254: 5-Cl-6-S (O) CF3-3-Py], [3255: 2-Me-6-6. S (O) CF3-3-Py], [3256: 4-Me-6-S (O) CF3-3-Py], [3257: 5-Me-6-S (O) CF3-3-Py] [3258: 2-CF3-6-S (O) CF3-3-Py], [3259: 4-CF3-6-S (O) CF3-3-Py], [3260: 5-CF3-6 S (O) CF3-3-Py], [3261: 2-CN-6-S (O) CF3-3-Py], [3262: 4-CN-6-S (O) C 3-3-3-Py], [3263: 5-CN-6-S (O) CF3-3-Py], [3264: 2-OMe-6-S (O) CF3-3-Py], [3265: 4-OMe-6-S (O) CF3-3-Py], [3266: 5-OMe-6-S (O) CF3-3-Py], [3267: 2-S (O) 2Me-3- Py], [3268: 4-Cl-2-S (O) 2Me-3-Py], [3269: 5-Cl-2-S (O) 2Me-3-Py], [3270: 6-Cl- 2-S (O) 2Me-3-Py], [3271: 4-Me-2-S (O) 2Me-3-Py], [3272: 5-Me-2-S (O) 2Me-3- Py], [3273: 6-Me-2-S (O) 2Me-3-Py], [3274: 4-CF3-2-S (O) 2Me-3-Py], [3 275: 5-CF3-2-S (O) 2Me-3-Py], [3276: 6-CF3-2-S (O) 2Me-3-Py], [3277: 4-CN-2-S ( O) 2Me-3-Py], [3278: 5-CN-2-S (O) 2Me-3-Py], [3279: 6-CN-2-S (O) 2Me-3-Py], [ 3280: 4-OMe-2-S (O) 2Me-3-Py], [3281: 5-OMe-2-S (O) 2Me-3-Py], [3282: 6-OMe-2-S ( O) 2Me-3-Py], [3283: 4-S (O) 2Me-3-Py], [3284: 2-Cl-4-S (O) 2Me-3-Py], [3285: 5- Cl-4-S (O) 2Me-3-Py], [3286: 6-Cl-4-S (O) 2Me-3-Py], [3287: 2-Me- -S (O) 2Me-3-Py], [3288: 5-Me-4-S (O) 2Me-3-Py], [3289: 6-Me-4-S (O) 2Me-3-Py ], [3290: 2-CF3-4-S (O) 2Me-3-Py], [3291: 5-CF3-4-S (O) 2Me-3-Py], [3292: 6-CF3-4]. -S (O) 2Me-3-Py], [3293: 2-CN-4-S (O) 2Me-3-Py], [3294: 5-CN-4-S (O) 2Me-3-Py ], [3295: 6-CN-4-S (O) 2Me-3-Py], [3296: 2-OMe-4-S (O) 2Me-3-Py], [3297: 5-OMe-4 -S (O) 2Me-3-Py], [3298: 6-OMe-4-S (O) 2Me-3-Py], [3299: 5-S (O) 2M -3-Py], [3300: 2-Cl-5-S (O) 2Me-3-Py],
[3301:4−Cl−5−S(O)2Me−3−Py]、[3302:6−Cl−5−S(O)2Me−3−Py]、[3303:2−Me−5−S(O)2Me−3−Py]、[3304:4−Me−5−S(O)2Me−3−Py]、[3305:6−Me−5−S(O)2Me−3−Py]、[3306:2−CF3−5−S(O)2Me−3−Py]、[3307:4−CF3−5−S(O)2Me−3−Py]、[3308:6−CF3−5−S(O)2Me−3−Py]、[3309:2−CN−5−S(O)2Me−3−Py]、[3310:4−CN−5−S(O)2Me−3−Py]、[3311:6−CN−5−S(O)2Me−3−Py]、[3312:2−OMe−5−S(O)2Me−3−Py]、[3313:4−OMe−5−S(O)2Me−3−Py]、[3314:6−OMe−5−S(O)2Me−3−Py]、[3315:6−S(O)2Me−3−Py]、[3316:2−Cl−6−S(O)2Me−3−Py]、[3317:4−Cl−6−S(O)2Me−3−Py]、[3318:5−Cl−6−S(O)2Me−3−Py]、[3319:2−Me−6−S(O)2Me−3−Py]、[3320:4−Me−6−S(O)2Me−3−Py]、[3321:5−Me−6−S(O)2Me−3−Py]、[3322:2−CF3−6−S(O)2Me−3−Py]、[3323:4−CF3−6−S(O)2Me−3−Py]、[3324:5−CF3−6−S(O)2Me−3−Py]、[3325:2−CN−6−S(O)2Me−3−Py]、[3326:4−CN−6−S(O)2Me−3−Py]、[3327:5−CN−6−S(O)2Me−3−Py]、[3328:2−OMe−6−S(O)2Me−3−Py]、[3329:4−OMe−6−S(O)2Me−3−Py]、[3330:5−OMe−6−S(O)2Me−3−Py]、[3331:2−S(O)2CF3−3−Py]、[3332:4−Cl−2−S(O)2CF3−3−Py]、[3333:5−Cl−2−S(O)2CF3−3−Py]、[3334:6−Cl−2−S(O)2CF3−3−Py]、[3335:4−Me−2−S(O)2CF3−3−Py]、[3336:5−Me−2−S(O)2CF3−3−Py]、[3337:6−Me−2−S(O)2CF3−3−Py]、[3338:4−CF3−2−S(O)2CF3−3−Py]、[3339:5−CF3−2−S(O)2CF3−3−Py]、[3340:6−CF3−2−S(O)2CF3−3−Py]、[3341:4−CN−2−S(O)2CF3−3−Py]、[3342:5−CN−2−S(O)2CF3−3−Py]、[3343:6−CN−2−S(O)2CF3−3−Py]、[3344:4−OMe−2−S(O)2CF3−3−Py]、[3345:5−OMe−2−S(O)2CF3−3−Py]、[3346:6−OMe−2−S(O)2CF3−3−Py]、[3347:4−S(O)2CF3−3−Py]、[3348:2−Cl−4−S(O)2CF3−3−Py]、[3349:5−Cl−4−S(O)2CF3−3−Py]、[3350:6−Cl−4−S(O)2CF3−3−Py]、[3351:2−Me−4−S(O)2CF3−3−Py]、[3352:5−Me−4−S(O)2CF3−3−Py]、[3353:6−Me−4−S(O)2CF3−3−Py]、[3354:2−CF3−4−S(O)2CF3−3−Py]、[3355:5−CF3−4−S(O)2CF3−3−Py]、[3356:6−CF3−4−S(O)2CF3−3−Py]、[3357:2−CN−4−S(O)2CF3−3−Py]、[3358:5−CN−4−S(O)2CF3−3−Py]、[3359:6−CN−4−S(O)2CF3−3−Py]、[3360:2−OMe−4−S(O)2CF3−3−Py]、[3361:5−OMe−4−S(O)2CF3−3−Py]、[3362:6−OMe−4−S(O)2CF3−3−Py]、[3363:5−S(O)2CF3−3−Py]、[3364:2−Cl−5−S(O)2CF3−3−Py]、[3365:4−Cl−5−S(O)2CF3−3−Py]、[3366:6−Cl−5−S(O)2CF3−3−Py]、[3367:2−Me−5−S(O)2CF3−3−Py]、[3368:4−Me−5−S(O)2CF3−3−Py]、[3369:6−Me−5−S(O)2CF3−3−Py]、[3370:2−CF3−5−S(O)2CF3−3−Py]、[3371:4−CF3−5−S(O)2CF3−3−Py]、[3372:6−CF3−5−S(O)2CF3−3−Py]、[3373:2−CN−5−S(O)2CF3−3−Py]、[3374:4−CN−5−S(O)2CF3−3−Py]、[3375:6−CN−5−S(O)2CF3−3−Py]、[3376:2−OMe−5−S(O)2CF3−3−Py]、[3377:4−OMe−5−S(O)2CF3−3−Py]、[3378:6−OMe−5−S(O)2CF3−3−Py]、[3379:6−S(O)2CF3−3−Py]、[3380:2−Cl−6−S(O)2CF3−3−Py]、[3381:4−Cl−6−S(O)2CF3−3−Py]、[3382:5−Cl−6−S(O)2CF3−3−Py]、[3383:2−Me−6−S(O)2CF3−3−Py]、[3384:4−Me−6−S(O)2CF3−3−Py]、[3385:5−Me−6−S(O)2CF3−3−Py]、[3386:2−CF3−6−S(O)2CF3−3−Py]、[3387:4−CF3−6−S(O)2CF3−3−Py]、[3388:5−CF3−6−S(O)2CF3−3−Py]、[3389:2−CN−6−S(O)2CF3−3−Py]、[3390:4−CN−6−S(O)2CF3−3−Py]、[3391:5−CN−6−S(O)2CF3−3−Py]、[3392:2−OMe−6−S(O)2CF3−3−Py]、[3393:4−OMe−6−S(O)2CF3−3−Py]、[3394:5−OMe−6−S(O)2CF3−3−Py]
[3395:2−CN−3−Py]、[3396:4−Cl−2−CN−3−Py]、[3397:5−Cl−2−CN−3−Py]、[3398:6−Cl−2−CN−3−Py]、[3399:4−Me−2−CN−3−Py]、[3400:5−Me−2−CN−3−Py]、[3301: 4-Cl-5-S (O) 2Me-3-Py], [3302: 6-Cl-5-S (O) 2Me-3-Py], [3303: 2-Me-5-S (O) 2Me-3-Py], [3304: 4-Me-5-S (O) 2Me-3-Py], [3305: 6-Me-5-S (O) 2Me-3-Py], [3306: 2-CF3-5-S (O) 2Me-3-Py], [3307: 4-CF3-5-S (O) 2Me-3-Py], [3308: 6-CF3-5-S (O) 2Me-3-Py], [3309: 2-CN-5-S (O) 2Me-3-Py], [3310: 4-CN-5-S (O) 2Me-3-Py], [3311: 6-CN-5-S (O) 2Me-3-Py], [3312: 2-OMe-5-S (O) 2Me-3-Py], [3313 4-OMe-5-S (O) 2Me-3-Py], [3314: 6-OMe-5-S (O) 2Me-3-Py], [3315: 6-S (O) 2Me-3- Py], [3316: 2-Cl-6-S (O) 2Me-3-Py], [3317: 4-Cl-6-S (O) 2Me-3-Py], [3318: 5-Cl- 6-S (O) 2Me-3-Py], [3319: 2-Me-6-S (O) 2Me-3-Py], [3320: 4-Me-6-S (O) 2Me-3- Py], [3321: 5-Me-6-S (O) 2Me-3-Py], [3322: 2-CF3-6-S (O) 2Me-3-Py], [3323: 4-CF3- 6-S (O) 2Me-3-Py], [3324: 5-CF3-6-S (O) 2Me-3-Py], [3325: 2-CN-6-S O) 2Me-3-Py], [3326: 4-CN-6-S (O) 2Me-3-Py], [3327: 5-CN-6-S (O) 2Me-3-Py], [ 3328: 2-OMe-6-S (O) 2Me-3-Py], [3329: 4-OMe-6-S (O) 2Me-3-Py], [3330: 5-OMe-6-S ( O) 2Me-3-Py], [3331: 2-S (O) 2CF3-3-Py], [3332: 4-Cl-2-S (O) 2CF3-3-Py], [3333: 5- Cl-2-S (O) 2CF3-3-Py], [3334: 6-Cl-2-S (O) 2CF3-3-Py], [3335: 4-Me-2-S (O) 2CF3- 3-Py], [3336: 5-Me-2-S (O) 2CF3-3-Py], [3337: 6-Me-2-S (O) 2CF 3-3-Py], [3338: 4-CF3-2-S (O) 2CF3-3-Py], [3339: 5-CF3-2-S (O) 2CF3-3-Py], [3340: 6-CF3-2-S (O) 2CF3-3-Py], [3341: 4-CN-2-S (O) 2CF3-3-Py], [3342: 5-CN-2-S (O) 2CF3-3-Py], [3343: 6-CN-2-S (O) 2CF3-3-Py], [3344: 4-OMe-2-S (O) 2CF3-3-Py], [3345: 5-OMe-2-S (O) 2CF3-3-Py], [3346: 6-OMe-2-S (O) 2CF3-3-Py], [3347: 4-S (O) 2CF3-3 Py], [3348: 2-Cl-4-S (O) 2CF3-3-Py], [3349: 5-Cl-4-S (O 2CF3-3-Py], [3350: 6-Cl-4-S (O) 2CF3-3-Py], [3351: 2-Me-4-S (O) 2CF3-3-Py], [3352: 5-Me-4-S (O) 2CF3-3-Py], [3353: 6-Me-4-S (O) 2CF3-3-Py], [3354: 2-CF3-4-S (O) 2CF3-3-Py], [3355: 5-CF3-4-S (O) 2CF3-3-Py], [3356: 6-CF3-4-S (O) 2CF3-3-Py], [3357: 2-CN-4-S (O) 2CF3-3-Py], [3358: 5-CN-4-S (O) 2CF3-3-Py], [3359: 6-CN-4-S (O) 2CF3-3-Py], [3360: 2-OMe-4-S (O) 2CF3-3-Py], [3361: 5-O e-4-S (O) 2CF3-3-Py], [3362: 6-OMe-4-S (O) 2CF3-3-Py], [3363: 5-S (O) 2CF3-3-Py] [3364: 2-Cl-5-S (O) 2CF3-3-Py], [3365: 4-Cl-5-S (O) 2CF3-3-Py], [3366: 6-Cl-5- S (O) 2CF3-3-Py], [3367: 2-Me-5-S (O) 2CF3-3-Py], [3368: 4-Me-5-S (O) 2CF3-3-Py] [3369: 6-Me-5-S (O) 2CF3-3-Py], [3370: 2-CF3-5-S (O) 2CF3-3-Py], [3371: 4-CF3-5 S (O) 2CF3-3-Py], [3372: 6-CF3-5-S (O) 2CF3-3-Py], [3373: 2 -CN-5-S (O) 2CF3-3-Py], [3374: 4-CN-5-S (O) 2CF3-3-Py], [3375: 6-CN-5-S (O) 2CF3 -3-Py], [3376: 2-OMe-5-S (O) 2CF3-3-Py], [3377: 4-OMe-5-S (O) 2CF3-3-Py], [3378: 6. -OMe-5-S (O) 2CF3-3-Py], [3379: 6-S (O) 2CF3-3-Py], [3380: 2-Cl-6-S (O) 2CF3-3-Py ], [3381: 4-Cl-6-S (O) 2CF3-3-Py], [3382: 5-Cl-6-S (O) 2CF3-3-Py], [3383: 2-Me-6. -S (O) 2CF3-3-Py], [3384: 4-Me-6-S (O) 2CF3-3-Py], [3385: -Me-6-S (O) 2CF3-3-Py], [3386: 2-CF3-6-S (O) 2CF3-3-Py], [3387: 4-CF3-6-S (O) 2CF3 -3-Py], [3388: 5-CF3-6-S (O) 2CF3-3-Py], [3389: 2-CN-6-S (O) 2CF3-3-Py], [3390: 4 -CN-6-S (O) 2CF3-3-Py], [3391: 5-CN-6-S (O) 2CF3-3-Py], [3392: 2-OMe-6-S (O) 2CF3 -3-Py], [3393: 4-OMe-6-S (O) 2CF3-3-Py], [3394: 5-OMe-6-S (O) 2CF3-3-Py]
[3395: 2-CN-3-Py], [3396: 4-Cl-2-CN-3-Py], [397: 5-Cl-2-CN-3-Py], [3398: 6-Cl -2-CN-3-Py], [3399: 4-Me-2-CN-3-Py], [3400: 5-Me-2-CN-3-Py],
[3401:6−Me−2−CN−3−Py]、[3402:4−CF3−2−CN−3−Py]、[3403:5−CF3−2−CN−3−Py]、[3404:6−CF3−2−CN−3−Py]、[3405:4−CN−2−CN−3−Py]、[3406:5−CN−2−CN−3−Py]、[3407:6−CN−2−CN−3−Py]、[3408:4−OMe−2−CN−3−Py]、[3409:5−OMe−2−CN−3−Py]、[3410:6−OMe−2−CN−3−Py]、[3411:4−CN−3−Py]、[3412:2−Cl−4−CN−3−Py]、[3413:5−Cl−4−CN−3−Py]、[3414:6−Cl−4−CN−3−Py]、[3415:2−Me−4−CN−3−Py]、[3416:5−Me−4−CN−3−Py]、[3417:6−Me−4−CN−3−Py]、[3418:2−CF3−4−CN−3−Py]、[3419:5−CF3−4−CN−3−Py]、[3420:6−CF3−4−CN−3−Py]、[3421:2−CN−4−CN−3−Py]、[3422:5−CN−4−CN−3−Py]、[3423:6−CN−4−CN−3−Py]、[3424:2−OMe−4−CN−3−Py]、[3425:5−OMe−4−CN−3−Py]、[3426:6−OMe−4−CN−3−Py]、[3427:5−CN−3−Py]、[3428:2−Cl−5−CN−3−Py]、[3429:4−Cl−5−CN−3−Py]、[3430:6−Cl−5−CN−3−Py]、[3431:2−Me−5−CN−3−Py]、[3432:4−Me−5−CN−3−Py]、[3433:6−Me−5−CN−3−Py]、[3434:2−CF3−5−CN−3−Py]、[3435:4−CF3−5−CN−3−Py]、[3436:6−CF3−5−CN−3−Py]、[3437:2−CN−5−CN−3−Py]、[3438:4−CN−5−CN−3−Py]、[3439:6−CN−5−CN−3−Py]、[3440:2−OMe−5−CN−3−Py]、[3441:4−OMe−5−CN−3−Py]、[3442:6−OMe−5−CN−3−Py]、[3443:6−CN−3−Py]、[3444:2−Cl−6−CN−3−Py]、[3445:4−Cl−6−CN−3−Py]、[3446:5−Cl−6−CN−3−Py]、[3447:2−Me−6−CN−3−Py]、[3448:4−Me−6−CN−3−Py]、[3449:5−Me−6−CN−3−Py]、[3450:2−CF3−6−CN−3−Py]、[3451:4−CF3−6−CN−3−Py]、[3452:5−CF3−6−CN−3−Py]、[3453:2−CN−6−CN−3−Py]、[3454:4−CN−6−CN−3−Py]、[3455:5−CN−6−CN−3−Py]、[3456:2−OMe−6−CN−3−Py]、[3457:4−OMe−6−CN−3−Py]、[3458:5−OMe−6−CN−3−Py]、[3459:2−COOMe−3−Py]、[3460:4−Cl−2−COOMe−3−Py]、[3461:5−Cl−2−COOMe−3−Py]、[3462:6−Cl−2−COOMe−3−Py]、[3463:4−Me−2−COOMe−3−Py]、[3464:5−Me−2−COOMe−3−Py]、[3465:6−Me−2−COOMe−3−Py]、[3466:4−CF3−2−COOMe−3−Py]、[3467:5−CF3−2−COOMe−3−Py]、[3468:6−CF3−2−COOMe−3−Py]、[3469:4−CN−2−COOMe−3−Py]、[3470:5−CN−2−COOMe−3−Py]、[3471:6−CN−2−COOMe−3−Py]、[3472:4−OMe−2−COOMe−3−Py]、[3473:5−OMe−2−COOMe−3−Py]、[3474:6−OMe−2−COOMe−3−Py]、[3475:4−COOMe−3−Py]、[3476:2−Cl−4−COOMe−3−Py]、[3477:5−Cl−4−COOMe−3−Py]、[3478:6−Cl−4−COOMe−3−Py]、[3479:2−Me−4−COOMe−3−Py]、[3480:5−Me−4−COOMe−3−Py]、[3481:6−Me−4−COOMe−3−Py]、[3482:2−CF3−4−COOMe−3−Py]、[3483:5−CF3−4−COOMe−3−Py]、[3484:6−CF3−4−COOMe−3−Py]、[3485:2−CN−4−COOMe−3−Py]、[3486:5−CN−4−COOMe−3−Py]、[3487:6−CN−4−COOMe−3−Py]、[3488:2−OMe−4−COOMe−3−Py]、[3489:5−OMe−4−COOMe−3−Py]、[3490:6−OMe−4−COOMe−3−Py]、[3491:5−COOMe−3−Py]、[3492:2−Cl−5−COOMe−3−Py]、[3493:4−Cl−5−COOMe−3−Py]、[3494:6−Cl−5−COOMe−3−Py]、[3495:2−Me−5−COOMe−3−Py]、[3496:4−Me−5−COOMe−3−Py]、[3497:6−Me−5−COOMe−3−Py]、[3498:2−CF3−5−COOMe−3−Py]、[3499:4−CF3−5−COOMe−3−Py]、[3500:6−CF3−5−COOMe−3−Py]、 [3401: 6-Me-2-CN-3-Py], [3402: 4-CF3-2-CN-3-Py], [3403: 5-CF3-2-CN-3-Py], [3404 : 6-CF3-2-CN-3-Py], [3405: 4-CN-2-CN-3-Py], [3406: 5-CN-2-CN-3-Py], [3407: 6 -CN-2-CN-3-Py], [3408: 4-OMe-2-CN-3-Py], [3409: 5-OMe-2-CN-3-Py], [3410: 6-OMe -2-CN-3-Py], [3411: 4-CN-3-Py], [3412: 2-Cl-4-CN-3-Py], [3413: 5-Cl-4-CN-3 -Py], [3414: 6-Cl-4-CN-3-Py], [3415: 2-Me-4-CN-3-Py], [3 16: 5-Me-4-CN-3-Py], [3417: 6-Me-4-CN-3-Py], [3418: 2-CF3-4-CN-3-Py], [3419: 5-CF3-4-CN-3-Py], [3420: 6-CF3-4-CN-3-Py], [3421: 2-CN-4-CN-3-Py], [3422: 5- CN-4-CN-3-Py], [3423: 6-CN-4-CN-3-Py], [3424: 2-OMe-4-CN-3-Py], [3425: 5-OMe- 4-CN-3-Py], [3426: 6-OMe-4-CN-3-Py], [3427: 5-CN-3-Py], [3428: 2-Cl-5-CN-3- Py], [3429: 4-Cl-5-CN-3-Py], [3430: 6-Cl-5-CN-3-Py], [343 : 2-Me-5-CN-3-Py], [3432: 4-Me-5-CN-3-Py], [3433: 6-Me-5-CN-3-Py], [3434: 2] -CF3-5-CN-3-Py], [3435: 4-CF3-5-CN-3-Py], [3436: 6-CF3-5-CN-3-Py], [3437: 2-CN -5-CN-3-Py], [3438: 4-CN-5-CN-3-Py], [3439: 6-CN-5-CN-3-Py], [3440: 2-OMe-5. -CN-3-Py], [3441: 4-OMe-5-CN-3-Py], [3442: 6-OMe-5-CN-3-Py], [3443: 6-CN-3-Py] ], [3444: 2-Cl-6-CN-3-Py], [3445: 4-Cl-6-CN-3-Py], [3446: 5 -Cl-6-CN-3-Py], [3447: 2-Me-6-CN-3-Py], [3448: 4-Me-6-CN-3-Py], [3449: 5-Me -6-CN-3-Py], [3450: 2-CF3-6-CN-3-Py], [3451: 4-CF3-6-CN-3-Py], [3452: 5-CF3-6 -CN-3-Py], [3453: 2-CN-6-CN-3-Py], [3454: 4-CN-6-CN-3-Py], [3455: 5-CN-6-CN -3-Py], [3456: 2-OMe-6-CN-3-Py], [3457: 4-OMe-6-CN-3-Py], [3458: 5-OMe-6-CN-3 -Py], [3459: 2-COOMe-3-Py], [3460: 4-Cl-2-COOMe-3-Py], [34 1: 5-Cl-2-COOMe-3-Py], [3462: 6-Cl-2-COOMe-3-Py], [3463: 4-Me-2-COOMe-3-Py], [3464: 5-Me-2-COOMe-3-Py], [3465: 6-Me-2-COOMe-3-Py], [3466: 4-CF3-2-COOMe-3-Py], [3467: 5- CF3-2-COOMe-3-Py], [3468: 6-CF3-2-COOMe-3-Py], [3469: 4-CN-2-COOMe-3-Py], [3470: 5-CN- 2-COOMe-3-Py], [3471: 6-CN-2-COOMe-3-Py], [3472: 4-OMe-2-COOMe-3-Py], [3473: 5-OMe-2- COOMe-3-Py], [3474: -OMe-2-COOMe-3-Py], [3475: 4-COOMe-3-Py], [3476: 2-Cl-4-COOMe-3-Py], [3477: 5-Cl-4-COOMe -3-Py], [3478: 6-Cl-4-COOMe-3-Py], [3479: 2-Me-4-COOMe-3-Py], [3480: 5-Me-4-COOMe-3 -Py], [3481: 6-Me-4-COOMe-3-Py], [3482: 2-CF3-4-COOMe-3-Py], [3483: 5-CF3-4-COOMe-3-Py ], [3484: 6-CF3-4-COOMe-3-Py], [3485: 2-CN-4-COOMe-3-Py], [3486: 5-CN-4-COOMe-3-Py], [3487: 6-CN-4-COO Me-3-Py], [3488: 2-OMe-4-COOMe-3-Py], [3289: 5-OMe-4-COOMe-3-Py], [3490: 6-OMe-4-COOMe- 3-Py], [3491: 5-COOMe-3-Py], [3492: 2-Cl-5-COOMe-3-Py], [3493: 4-Cl-5-COOMe-3-Py], [ 3494: 6-Cl-5-COOMe-3-Py], [3495: 2-Me-5-COOMe-3-Py], [3496: 4-Me-5-COOMe-3-Py], [3497: 6-Me-5-COOMe-3-Py], [3498: 2-CF3-5-COOMe-3-Py], [3499: 4-CF3-5-COOMe-3-Py], [3500: 6- CF3-5-COOMe-3-Py ,
[3501:2−CN−5−COOMe−3−Py]、[3502:4−CN−5−COOMe−3−Py]、[3503:6−CN−5−COOMe−3−Py]、[3504:2−OMe−5−COOMe−3−Py]、[3505:4−OMe−5−COOMe−3−Py]、[3506:6−OMe−5−COOMe−3−Py]、[3507:6−COOMe−3−Py]、[3508:2−Cl−6−COOMe−3−Py]、[3509:4−Cl−6−COOMe−3−Py]、[3510:5−Cl−6−COOMe−3−Py]、[3511:2−Me−6−COOMe−3−Py]、[3512:4−Me−6−COOMe−3−Py]、[3513:5−Me−6−COOMe−3−Py]、[3514:2−CF3−6−COOMe−3−Py]、[3515:4−CF3−6−COOMe−3−Py]、[3516:5−CF3−6−COOMe−3−Py]、[3517:2−CN−6−COOMe−3−Py]、[3518:4−CN−6−COOMe−3−Py]、[3519:5−CN−6−COOMe−3−Py]、[3520:2−OMe−6−COOMe−3−Py]、[3521:4−OMe−6−COOMe−3−Py]、[3522:5−OMe−6−COOMe−3−Py]、[3523:2−NO2−3−Py]、[3524:4−Cl−2−NO2−3−Py]、[3525:5−Cl−2−NO2−3−Py]、[3526:6−Cl−2−NO2−3−Py]、[3527:4−Me−2−NO2−3−Py]、[3528:5−Me−2−NO2−3−Py]、[3529:6−Me−2−NO2−3−Py]、[3530:4−CF3−2−NO2−3−Py]、[3531:5−CF3−2−NO2−3−Py]、[3532:6−CF3−2−NO2−3−Py]、[3533:4−CN−2−NO2−3−Py]、[3534:5−CN−2−NO2−3−Py]、[3535:6−CN−2−NO2−3−Py]、[3536:4−OMe−2−NO2−3−Py]、[3537:5−OMe−2−NO2−3−Py]、[3538:6−OMe−2−NO2−3−Py]、[3539:4−NO2−3−Py]、[3540:2−Cl−4−NO2−3−Py]、[3541:5−Cl−4−NO2−3−Py]、[3542:6−Cl−4−NO2−3−Py]、[3543:2−Me−4−NO2−3−Py]、[3544:5−Me−4−NO2−3−Py]、[3545:6−Me−4−NO2−3−Py]、[3546:2−CF3−4−NO2−3−Py]、[3547:5−CF3−4−NO2−3−Py]、[3548:6−CF3−4−NO2−3−Py]、[3549:2−CN−4−NO2−3−Py]、[3550:5−CN−4−NO2−3−Py]、[3551:6−CN−4−NO2−3−Py]、[3552:2−OMe−4−NO2−3−Py]、[3553:5−OMe−4−NO2−3−Py]、[3554:6−OMe−4−NO2−3−Py]、[3555:5−NO2−3−Py]、[3556:2−Cl−5−NO2−3−Py]、[3557:4−Cl−5−NO2−3−Py]、[3558:6−Cl−5−NO2−3−Py]、[3559:2−Me−5−NO2−3−Py]、[3560:4−Me−5−NO2−3−Py]、[3561:6−Me−5−NO2−3−Py]、[3562:2−CF3−5−NO2−3−Py]、[3563:4−CF3−5−NO2−3−Py]、[3564:6−CF3−5−NO2−3−Py]、[3565:2−CN−5−NO2−3−Py]、[3566:4−CN−5−NO2−3−Py]、[3567:6−CN−5−NO2−3−Py]、[3568:2−OMe−5−NO2−3−Py]、[3569:4−OMe−5−NO2−3−Py]、[3570:6−OMe−5−NO2−3−Py]、[3571:6−NO2−3−Py]、[3572:2−Cl−6−NO2−3−Py]、[3573:4−Cl−6−NO2−3−Py]、[3574:5−Cl−6−NO2−3−Py]、[3575:2−Me−6−NO2−3−Py]、[3576:4−Me−6−NO2−3−Py]、[3577:5−Me−6−NO2−3−Py]、[3578:2−CF3−6−NO2−3−Py]、[3579:4−CF3−6−NO2−3−Py]、[3580:5−CF3−6−NO2−3−Py]、[3581:2−CN−6−NO2−3−Py]、[3582:4−CN−6−NO2−3−Py]、[3583:5−CN−6−NO2−3−Py]、[3584:2−OMe−6−NO2−3−Py]、[3585:4−OMe−6−NO2−3−Py]、[3586:5−OMe−6−NO2−3−Py]、[3587:2−NH2−3−Py]、[3588:4−Cl−2−NH2−3−Py]、[3589:5−Cl−2−NH2−3−Py]、[3590:6−Cl−2−NH2−3−Py]、[3591:4−Me−2−NH2−3−Py]、[3592:5−Me−2−NH2−3−Py]、[3593:6−Me−2−NH2−3−Py]、[3594:4−CF3−2−NH2−3−Py]、[3595:5−CF3−2−NH2−3−Py]、[3596:6−CF3−2−NH2−3−Py]、[3597:4−CN−2−NH2−3−Py]、[3598:5−CN−2−NH2−3−Py]、[3599:6−CN−2−NH2−3−Py]、[3600:4−OMe−2−NH2−3−Py]、 [3501: 2-CN-5-COOMe-3-Py], [3502: 4-CN-5-COOMe-3-Py], [3503: 6-CN-5-COOMe-3-Py], [3504 : 2-OMe-5-COOMe-3-Py], [3505: 4-OMe-5-COOMe-3-Py], [3506: 6-OMe-5-COOMe-3-Py], [3507: 6 -COOMe-3-Py], [3508: 2-Cl-6-COOMe-3-Py], [3509: 4-Cl-6-COOMe-3-Py], [3510: 5-Cl-6-COOMe -3-Py], [3511: 2-Me-6-COOMe-3-Py], [3512: 4-Me-6-COOMe-3-Py], [3513: 5-Me-6-COOMe-3. -Py], [3514: 2-CF -6-COOMe-3-Py], [3515: 4-CF3-6-COOMe-3-Py], [3516: 5-CF3-6-COOMe-3-Py], [3517: 2-CN-6 -COOMe-3-Py], [3518: 4-CN-6-COOMe-3-Py], [3519: 5-CN-6-COOMe-3-Py], [3520: 2-OMe-6-COOMe -3-Py], [3521: 4-OMe-6-COOMe-3-Py], [3522: 5-OMe-6-COOMe-3-Py], [3523: 2-NO2-3-Py], [3524: 4-Cl-2-NO2-3-Py], [3525: 5-Cl-2-NO2-3-Py], [3526: 6-Cl-2-NO2-3-Py], [3527 : 4-Me-2-NO2-3-Py], [3 28: 5-Me-2-NO2-3-Py], [3529: 6-Me-2-NO2-3-Py], [3530: 4-CF3-2-NO2-3-Py], [3531: 5-CF3-2-NO2-3-Py], [3532: 6-CF3-2-NO2-3-Py], [3533: 4-CN-2-NO2-3-Py], [3534: 5- CN-2-NO2-3-Py], [3535: 6-CN-2-NO2-3-Py], [3536: 4-OMe-2-NO2-3-Py], [3537: 5-OMe- 2-NO2-3-Py], [3538: 6-OMe-2-NO2-3-Py], [3539: 4-NO2-3-Py], [3540: 2-Cl-4-NO2-3- Py], [3541: 5-Cl-4-NO2-3-Py], [3542: 6-Cl-4- NO2-3-Py], [3543: 2-Me-4-NO2-3-Py], [3544: 5-Me-4-NO2-3-Py], [3545: 6-Me-4-NO2- 3-Py], [3546: 2-CF3-4-NO2-3-Py], [3547: 5-CF3-4-NO2-3-Py], [3548: 6-CF3-4-NO2-3- Py], [3549: 2-CN-4-NO2-3-Py], [3550: 5-CN-4-NO2-3-Py], [3551: 6-CN-4-NO2-3-Py] [3552: 2-OMe-4-NO2-3-Py], [3553: 5-OMe-4-NO2-3-Py], [3554: 6-OMe-4-NO2-3-Py], [ 3555: 5-NO2-3-Py], [3556: 2-Cl-5-NO2-3-Py], 3557: 4-Cl-5-NO2-3-Py], [3558: 6-Cl-5-NO2-3-Py], [3559: 2-Me-5-NO2-3-Py], [3560: 4-Me-5-NO2-3-Py], [3561: 6-Me-5-NO2-3-Py], [3562: 2-CF3-5-NO2-3-Py], [3563: 4- CF3-5-NO2-3-Py], [3564: 6-CF3-5-NO2-3-Py], [3565: 2-CN-5-NO2-3-Py], [3566: 4-CN- 5-NO2-3-Py], [3567: 6-CN-5-NO2-3-Py], [3568: 2-OMe-5-NO2-3-Py], [3569: 4-OMe-5 NO2-3-Py], [3570: 6-OMe-5-NO2-3-Py], [3571 6-NO2-3-Py], [3572: 2-Cl-6-NO2-3-Py], [3573: 4-Cl-6-NO2-3-Py], [3574: 5-Cl-6 NO2-3-Py], [3575: 2-Me-6-NO2-3-Py], [3576: 4-Me-6-NO2-3-Py], [3577: 5-Me-6-NO2- 3-Py], [3578: 2-CF3-6-NO2-3-Py], [3579: 4-CF3-6-NO2-3-Py], [3580: 5-CF3-6-NO2-3- Py], [3581: 2-CN-6-NO2-3-Py], [3582: 4-CN-6-NO2-3-Py], [3583: 5-CN-6-NO2-3-Py] [3584: 2-OMe-6-NO2-3-Py], [3585: 4-OMe-6-NO2- 3-Py], [3586: 5-OMe-6-NO2-3-Py], [3587: 2-NH2-3-Py], [3588: 4-Cl-2-NH2-3-Py], [ 3589: 5-Cl-2-NH2-3-Py], [3590: 6-Cl-2-NH2-3-Py], [3591: 4-Me-2-NH2-3-Py], [3592: 5-Me-2-NH2-3-Py], [3593: 6-Me-2-NH2-3-Py], [3594: 4-CF3-2-NH2-3-Py], [3595: 5- CF3-2-NH2-3-Py], [3596: 6-CF3-2-NH2-3-Py], [3597: 4-CN-2-NH2-3-Py], [3598: 5-CN- 2-NH2-3-Py], [3599: 6-CN-2-NH2-3-Py], [3600: -OMe-2-NH2-3-Py],
[3601:5−OMe−2−NH2−3−Py]、[3602:6−OMe−2−NH2−3−Py]、[3603:4−NH2−3−Py]、[3604:2−Cl−4−NH2−3−Py]、[3605:5−Cl−4−NH2−3−Py]、[3606:6−Cl−4−NH2−3−Py]、[3607:2−Me−4−NH2−3−Py]、[3608:5−Me−4−NH2−3−Py]、[3609:6−Me−4−NH2−3−Py]、[3610:2−CF3−4−NH2−3−Py]、[3611:5−CF3−4−NH2−3−Py]、[3612:6−CF3−4−NH2−3−Py]、[3613:2−CN−4−NH2−3−Py]、[3614:5−CN−4−NH2−3−Py]、[3615:6−CN−4−NH2−3−Py]、[3616:2−OMe−4−NH2−3−Py]、[3617:5−OMe−4−NH2−3−Py]、[3618:6−OMe−4−NH2−3−Py]、[3619:5−NH2−3−Py]、[3620:2−Cl−5−NH2−3−Py]、[3621:4−Cl−5−NH2−3−Py]、[3622:6−Cl−5−NH2−3−Py]、[3623:2−Me−5−NH2−3−Py]、[3624:4−Me−5−NH2−3−Py]、[3625:6−Me−5−NH2−3−Py]、[3626:2−CF3−5−NH2−3−Py]、[3627:4−CF3−5−NH2−3−Py]、[3628:6−CF3−5−NH2−3−Py]、[3629:2−CN−5−NH2−3−Py]、[3630:4−CN−5−NH2−3−Py]、[3631:6−CN−5−NH2−3−Py]、[3632:2−OMe−5−NH2−3−Py]、[3633:4−OMe−5−NH2−3−Py]、[3634:6−OMe−5−NH2−3−Py]、[3635:6−NH2−3−Py]、[3636:2−Cl−6−NH2−3−Py]、[3637:4−Cl−6−NH2−3−Py]、[3638:5−Cl−6−NH2−3−Py]、[3639:2−Me−6−NH2−3−Py]、[3640:4−Me−6−NH2−3−Py]、[3641:5−Me−6−NH2−3−Py]、[3642:2−CF3−6−NH2−3−Py]、[3643:4−CF3−6−NH2−3−Py]、[3644:5−CF3−6−NH2−3−Py]、[3645:2−CN−6−NH2−3−Py]、[3646:4−CN−6−NH2−3−Py]、[3647:5−CN−6−NH2−3−Py]、[3648:2−OMe−6−NH2−3−Py]、[3649:4−OMe−6−NH2−3−Py]、[3650:5−OMe−6−NH2−3−Py]、[3651:2−NHMe−3−Py]、[3652:4−Cl−2−NHMe−3−Py]、[3653:5−Cl−2−NHMe−3−Py]、[3654:6−Cl−2−NHMe−3−Py]、[3655:4−Me−2−NHMe−3−Py]、[3656:5−Me−2−NHMe−3−Py]、[3657:6−Me−2−NHMe−3−Py]、[3658:4−CF3−2−NHMe−3−Py]、[3659:5−CF3−2−NHMe−3−Py]、[3660:6−CF3−2−NHMe−3−Py]、[3661:4−CN−2−NHMe−3−Py]、[3662:5−CN−2−NHMe−3−Py]、[3663:6−CN−2−NHMe−3−Py]、[3664:4−OMe−2−NHMe−3−Py]、[3665:5−OMe−2−NHMe−3−Py]、[3666:6−OMe−2−NHMe−3−Py]、[3667:4−NHMe−3−Py]、[3668:2−Cl−4−NHMe−3−Py]、[3669:5−Cl−4−NHMe−3−Py]、[3670:6−Cl−4−MHMe−3−Py]、[3671:2−Me−4−NHMe−3−Py]、[3672:5−Me−4−NHMe−3−Py]、[3673:6−Me−4−NHMe−3−Py]、[3674:2−CF3−4−NHMe−3−Py]、[3675:5−CF3−4−NHMe−3−Py]、[3676:6−CF3−4−NHMe−3−Py]、[3677:2−CN−4−NHMe−3−Py]、[3678:5−CN−4−NHMe−3−Py]、[3679:6−CN−4−NHMe−3−Py]、[3680:2−OMe−4−NHMe−3−Py]、[3681:5−OMe−4−NHMe−3−Py]、[3682:6−OMe−4−NHMe−3−Py]、[3683:5−NHMe−3−Py]、[3684:2−Cl−5−NHMe−3−Py]、[3685:4−Cl−5−NHMe−3−Py]、[3686:6−Cl−5−NHMe−3−Py]、[3687:2−Me−5−NHMe−3−Py]、[3688:4−Me−5−NHMe−3−Py]、[3689:6−Me−5−NHMe−3−Py]、[3690:2−CF3−5−NHMe−3−Py]、[3691:4−CF3−5−NHMe−3−Py]、[3692:6−CF3−5−NHMe−3−Py]、[3693:2−CN−5−NHMe−3−Py]、[3694:4−CN−5−NHMe−3−Py]、[3695:6−CN−5−NHMe−3−Py]、[3696:2−OMe−5−MHMe−3−Py]、[3697:4−OMe−5−NHMe−3−Py]、[3698:6−OMe−5−NHMe−3−Py]、[3699:6−NHMe−3−Py]、[3700:2−Cl−6−NHMe−3−Py]、 [3601: 5-OMe-2-NH2-3-Py], [3602: 6-OMe-2-NH2-3-Py], [3603: 4-NH2-3-Py], [3604: 2-Cl -4-NH2-3-Py], [3605: 5-Cl-4-NH2-3-Py], [3606: 6-Cl-4-NH2-3-Py], [3607: 2-Me-4 -NH2-3-Py], [3608: 5-Me-4-NH2-3-Py], [3609: 6-Me-4-NH2-3-Py], [3610: 2-CF3-4-NH2 -3-Py], [3611: 5-CF3-4-NH2-3-Py], [3612: 6-CF3-4-NH2-3-Py], [3613: 2-CN-4-NH2-3 -Py], [3614: 5-CN-4-NH2-3-Py], [3615: 6-CN- -NH2-3-Py], [3616: 2-OMe-4-NH2-3-Py], [3617: 5-OMe-4-NH2-3-Py], [3618: 6-OMe-4-NH2 -3-Py], [3619: 5-NH2-3-Py], [3620: 2-Cl-5-NH2-3-Py], [3621: 4-Cl-5-NH2-3-Py], [3622: 6-Cl-5-NH2-3-Py], [3623: 2-Me-5-NH2-3-Py], [3624: 4-Me-5-NH2-3-Py], [3625 : 6-Me-5-NH2-3-Py], [3626: 2-CF3-5-NH2-3-Py], [3627: 4-CF3-5-NH2-3-Py], [3628: 6 -CF3-5-NH2-3-Py], [3629: 2-CN-5-NH2-3-Py [3630: 4-CN-5-NH2-3-Py], [3631: 6-CN-5-NH2-3-Py], [3632: 2-OMe-5-NH2-3-Py], [ 3633: 4-OMe-5-NH2-3-Py], [3634: 6-OMe-5-NH2-3-Py], [3635: 6-NH2-3-Py], [3636: 2-Cl- 6-NH2-3-Py], [3637: 4-Cl-6-NH2-3-Py], [3638: 5-Cl-6-NH2-3-Py], [3639: 2-Me-6-6 NH2-3-Py], [3640: 4-Me-6-NH2-3-Py], [3641: 5-Me-6-NH2-3-Py], [3642: 2-CF3-6-NH2- 3-Py], [3643: 4-CF3-6-NH2-3-Py], [3644: 5-CF 3-6-NH2-3-Py], [3645: 2-CN-6-NH2-3-Py], [3646: 4-CN-6-NH2-3-Py], [3647: 5-CN- 6-NH2-3-Py], [3648: 2-OMe-6-NH2-3-Py], [3649: 4-OMe-6-NH2-3-Py], [3650: 5-OMe-6 NH2-3-Py], [3651: 2-NHMe-3-Py], [3652: 4-Cl-2-NHMe-3-Py], [3653: 5-Cl-2-NHMe-3-Py] [3654: 6-Cl-2-NHMe-3-Py], [3655: 4-Me-2-NHMe-3-Py], [3656: 5-Me-2-NHMe-3-Py], [ 3657: 6-Me-2-NHMe-3-Py], [3658: 4-CF3-2-N Me-3-Py], [3659: 5-CF3-2-NHMe-3-Py], [3660: 6-CF3-2-NHMe-3-Py], [3661: 4-CN-2-NHMe- 3-Py], [3662: 5-CN-2-NHMe-3-Py], [3663: 6-CN-2-NHMe-3-Py], [3664: 4-OMe-2-NHMe-3- Py], [3665: 5-OMe-2-NHMe-3-Py], [3666: 6-OMe-2-NHMe-3-Py], [3667: 4-NHMe-3-Py], [3668: 2-Cl-4-NHMe-3-Py], [3669: 5-Cl-4-NHMe-3-Py], [3670: 6-Cl-4-MHMe-3-Py], [3671: 2- Me-4-NHMe-3-Py], [3672: 5-Me- -NHMe-3-Py], [3673: 6-Me-4-NHMe-3-Py], [3674: 2-CF3-4-NHMe-3-Py], [3675: 5-CF3-4-NHMe -3-Py], [3676: 6-CF3-4-NHMe-3-Py], [3777: 2-CN-4-NHMe-3-Py], [3678: 5-CN-4-NHMe-3 -Py], [3679: 6-CN-4-NHMe-3-Py], [3680: 2-OMe-4-NHMe-3-Py], [3681: 5-OMe-4-NHMe-3-Py ], [3682: 6-OMe-4-NHMe-3-Py], [3683: 5-NHMe-3-Py], [3684: 2-Cl-5-NHMe-3-Py], [3685: 4] -Cl-5-NHMe-3-Py], [3686: 6- Cl-5-NHMe-3-Py], [3687: 2-Me-5-NHMe-3-Py], [3688: 4-Me-5-NHMe-3-Py], [3687: 6-Me- 5-NHMe-3-Py], [3690: 2-CF3-5-NHMe-3-Py], [3691: 4-CF3-5-NHMe-3-Py], [3692: 6-CF3-5 NHMe-3-Py], [3693: 2-CN-5-NHMe-3-Py], [3694: 4-CN-5-NHMe-3-Py], [3695: 6-CN-5-NHMe- 3-Py], [3696: 2-OMe-5-MHMe-3-Py], [3697: 4-OMe-5-NHMe-3-Py], [3698: 6-OMe-5-NHMe-3- Py], [3699: 6-NHMe-3-Py], [370 : 2-Cl-6-NHMe-3-Py],
[3701:4−Cl−6−NHMe−3−Py]、[3702:5−Cl−6−NHMe−3−Py]、[3703:2−Me−6−NHMe−3−Py]、[3704:4−Me−6−NHMe−3−Py]、[3705:5−Me−6−NHMe−3−Py]、[3706:2−CF3−6−NHMe−3−Py]、[3707:4−CF3−6−NHMe−3−Py]、[3708:5−CF3−6−NHMe−3−Py]、[3709:2−CN−6−NHMe−3−Py]、[3710:4−CN−6−NHMe−3−Py]、[3711:5−CN−6−NHMe−3−Py]、[3712:2−OMe−6−NHMe−3−Py]、[3713:4−OMe−6−NHMe−3−Py]、[3714:5−OMe−6−NHMe−3−Py]、[3715:2−NMe2−3−Py]、[3716:4−Cl−2−NMe2−3−Py]、[3717:5−Cl−2−NMe2−3−Py]、[3718:6−Cl−2−NMe2−3−Py]、[3719:4−Me−2−NMe2−3−Py]、[3720:5−Me−2−NMe2−3−Py]、[3721:6−Me−2−NMe2−3−Py]、[3722:4−CF3−2−NMe2−3−Py]、[3723:5−CF3−2−NMe2−3−Py]、[3724:6−CF3−2−NMe2−3−Py]、[3725:4−CN−2−NMe2−3−Py]、[3726:5−CN−2−NMe2−3−Py]、[3727:6−CN−2−NMe2−3−Py]、[3728:4−OMe−2−NMe2−3−Py]、[3729:5−OMe−2−NMe2−3−Py]、[3730:6−OMe−2−NMe2−3−Py]、[3731:4−NMe2−3−Py]、[3732:2−Cl−4−NMe2−3−Py]、[3733:5−Cl−4−NMe2−3−Py]、[3734:6−Cl−4−NMe2−3−Py]、[3735:2−Me−4−NMe2−3−Py]、[3736:5−Me−4−NMe2−3−Py]、[3737:6−Me−4−NMe2−3−Py]、[3738:2−CF3−4−NMe2−3−Py]、[3739:5−CF3−4−NMe2−3−Py]、[3740:6−CF3−4−NMe2−3−Py]、[3741:2−CN−4−NMe2−3−Py]、[3742:5−CN−4−NMe2−3−Py]、[3743:6−CN−4−NMe2−3−Py]、[3744:2−OMe−4−NMe2−3−Py]、[3745:5−OMe−4−NMe2−3−Py]、[3746:6−OMe−4−NMe2−3−Py]、[3747:5−NMe2−3−Py]、[3748:2−Cl−5−NMe2−3−Py]、[3749:4−Cl−5−NMe2−3−Py]、[3750:6−Cl−5−NMe2−3−Py]、[3751:2−Me−5−NMe2−3−Py]、[3752:4−Me−5−NMe2−3−Py]、[3753:6−Me−5−NMe2−3−Py]、[3754:2−CF3−5−NMe2−3−Py]、[3755:4−CF3−5−NMe2−3−Py]、[3756:6−CF3−5−NMe2−3−Py]、[3757:2−CN−5−NMe2−3−Py]、[3758:4−CN−5−NMe2−3−Py]、[3759:6−CN−5−NMe2−3−Py]、[3760:2−OMe−5−NMe2−3−Py]、[3761:4−OMe−5−NMe2−3−Py]、[3762:6−OMe−5−NMe2−3−Py]、[3763:6−NMe2−3−Py]、[3764:2−Cl−6−NMe2−3−Py]、[3765:4−Cl−6−NMe2−3−Py]、[3766:5−Cl−6−NMe2−3−Py]、[3767:2−Me−6−NMe2−3−Py]、[3768:4−Me−6−NMe2−3−Py]、[3769:5−Me−6−NMe2−3−Py]、[3770:2−CF3−6−NMe2−3−Py]、[3771:4−CF3−6−NMe2−3−Py]、[3772:5−CF3−6−NMe2−3−Py]、[3773:2−CN−6−NMe2−3−Py]、[3774:4−CN−6−NMe2−3−Py]、[3775:5−CN−6−NMe2−3−Py]、[3776:2−OMe−6−NMe2−3−Py]、[3777:4−OMe−6−NMe2−3−Py]、[3778:5−OMe−6−NMe2−3−Py]、[3779:2−ACNH−3−Py]、[3780:4−Cl−2−ACNH−3−Py]、[3781:5−Cl−2−ACNH−3−Py]、[3782:6−Cl−2−ACNH−3−Py]、[3783:4−Me−2−ACNH−3−Py]、[3784:5−Me−2−ACNH−3−Py]、[3785:6−Me−2−ACNH−3−Py]、[3786:4−CF3−2−ACNH−3−Py]、[3787:5−CF3−2−ACNH−3−Py]、[3788:6−CF3−2−ACNH−3−Py]、[3789:4−CN−2−ACNH−3−Py]、[3790:5−CN−2−ACNH−3−Py]、[3791:6−CN−2−ACNH−3−Py]、[3792:4−OMe−2−ACNH−3−Py]、[3793:5−OMe−2−ACNH−3−Py]、[3794:6−OMe−2−ACNH−3−Py]、[3795:4−ACNH−3−Py]、[3796:2−Cl−4−ACNH−3−Py]、[3797:5−Cl−4−ACNH−3−Py]、[3798:6−Cl−4−ACNH−3−Py]、[3799:2−Me−4−ACNH−3−Py]、[3800:5−Me−4−ACNH−3−Py]、 [3701: 4-Cl-6-NHMe-3-Py], [3702: 5-Cl-6-NHMe-3-Py], [3703: 2-Me-6-NHMe-3-Py], [3704 : 4-Me-6-NHMe-3-Py], [3705: 5-Me-6-NHMe-3-Py], [3706: 2-CF3-6-NHMe-3-Py], [3707: 4 -CF3-6-NHMe-3-Py], [3708: 5-CF3-6-NHMe-3-Py], [3709: 2-CN-6-NHMe-3-Py], [3710: 4-CN -6-NHMe-3-Py], [3711: 5-CN-6-NHMe-3-Py], [3712: 2-OMe-6-NHMe-3-Py], [3713: 4-OMe-6 -NHMe-3-Py], [3714: 5-OMe-6-NH e-3-Py], [3715: 2-NMe2-3-Py], [3716: 4-Cl-2-NMe2-3-Py], [3717: 5-Cl-2-NMe2-3-Py] [3718: 6-Cl-2-NMe2-3-Py], [3719: 4-Me-2-NMe2-3-Py], [3720: 5-Me-2-NMe2-3-Py], [ 3721: 6-Me-2-NMe2-3-Py], [3722: 4-CF3-2-NMe2-3-Py], [3723: 5-CF3-2-NMe2-3-Py], [3724: 6-CF3-2-NMe2-3-Py], [3725: 4-CN-2-NMe2-3-Py], [3726: 5-CN-2-NMe2-3-Py], [3727: 6- CN-2-NMe2-3-Py], [3728: 4-OMe-2- Me2-3-Py], [3729: 5-OMe-2-NMe2-3-Py], [3730: 6-OMe-2-NMe2-3-Py], [3731: 4-NMe2-3-Py] [3732: 2-Cl-4-NMe2-3-Py], [3733: 5-Cl-4-NMe2-3-Py], [3734: 6-Cl-4-NMe2-3-Py], [ 3735: 2-Me-4-NMe2-3-Py], [3736: 5-Me-4-NMe2-3-Py], [3737: 6-Me-4-NMe2-3-Py], [3738: 2-CF3-4-NMe2-3-Py], [3739: 5-CF3-4-NMe2-3-Py], [3740: 6-CF3-4-NMe2-3-Py], [3741: 2- CN-4-NMe2-3-Py], [3742: 5-CN- 4-NMe2-3-Py], [3743: 6-CN-4-NMe2-3-Py], [3744: 2-OMe-4-NMe2-3-Py], [3745: 5-OMe-4- NMe2-3-Py], [3746: 6-OMe-4-NMe2-3-Py], [3747: 5-NMe2-3-Py], [3748: 2-Cl-5-NMe2-3-Py] [3749: 4-Cl-5-NMe2-3-Py], [3750: 6-Cl-5-NMe2-3-Py], [3751: 2-Me-5-NMe2-3-Py], [ 3752: 4-Me-5-NMe2-3-Py], [3753: 6-Me-5-NMe2-3-Py], [3754: 2-CF3-5-NMe2-3-Py], [3755: 4-CF3-5-NMe2-3-Py], [3756: 6- F3-5-NMe2-3-Py], [3757: 2-CN-5-NMe2-3-Py], [3758: 4-CN-5-NMe2-3-Py], [3759: 6-CN- 5-NMe2-3-Py], [3760: 2-OMe-5-NMe2-3-Py], [3761: 4-OMe-5-NMe2-3-Py], [3762: 6-OMe-5 NMe2-3-Py], [3763: 6-NMe2-3-Py], [3764: 2-Cl-6-NMe2-3-Py], [3765: 4-Cl-6-NMe2-3-Py] [3766: 5-Cl-6-NMe2-3-Py], [3767: 2-Me-6-NMe2-3-Py], [3768: 4-Me-6-NMe2-3-Py], [ 3769: 5-Me-6-NMe2-3-Py], [3770: -CF3-6-NMe2-3-Py], [3771: 4-CF3-6-NMe2-3-Py], [3772: 5-CF3-6-NMe2-3-Py], [3773: 2-CN -6-NMe2-3-Py], [3774: 4-CN-6-NMe2-3-Py], [3775: 5-CN-6-NMe2-3-Py], [3776: 2-OMe-6 -NMe2-3-Py], [3777: 4-OMe-6-NMe2-3-Py], [3778: 5-OMe-6-NMe2-3-Py], [379: 2-ACNH-3-Py ], [3780: 4-Cl-2-ACNH-3-Py], [3781: 5-Cl-2-ACNH-3-Py], [3782: 6-Cl-2-ACNH-3-Py], [3783: 4-Me-2-ACNH-3-Py], [37 84: 5-Me-2-ACNH-3-Py], [3785: 6-Me-2-ACNH-3-Py], [3786: 4-CF3-2-ACNH-3-Py], [3787: 5-CF3-2-ACNH-3-Py], [3788: 6-CF3-2-ACNH-3-Py], [3789: 4-CN-2-ACNH-3-Py], [3790: 5- CN-2-ACNH-3-Py], [3791: 6-CN-2-ACNH-3-Py], [3792: 4-OMe-2-ACNH-3-Py], [3793: 5-OMe- 2-ACNH-3-Py], [3794: 6-OMe-2-ACNH-3-Py], [3795: 4-ACNH-3-Py], [3796: 2-Cl-4-ACNH-3- Py], [3797: 5-Cl-4-ACNH-3-Py] [3798: 6-Cl-4-ACNH-3-Py], [3799: 2-Me-4-ACNH-3-Py], [3800: 5-Me-4-ACNH-3-Py],
[3801:6−Me−4−ACNH−3−Py]、[3802:2−CF3−4−ACNH−3−Py]、[3803:5−CF3−4−ACNH−3−Py]、[3804:6−CF3−4−ACNH−3−Py]、[3805:2−CN−4−ACNH−3−Py]、[3806:5−CN−4−ACNH−3−Py]、[3807:6−CN−4−ACNH−3−Py]、[3808:2−OMe−4−ACNH−3−Py]、[3809:5−OMe−4−ACNH−3−Py]、[3810:6−OMe−4−ACNH−3−Py]、[3811:5−ACNH−3−Py]、[3812:2−Cl−5−ACNH−3−Py]、[3813:4−Cl−5−ACNH−3−Py]、[3814:6−Cl−5−ACNH−3−Py]、[3815:2−Me−5−ACNH−3−Py]、[3816:4−Me−5−ACNH−3−Py]、[3817:6−Me−5−ACNH−3−Py]、[3818:2−CF3−5−ACNH−3−Py]、[3819:4−CF3−5−ACNH−3−Py]、[3820:6−CF3−5−ACNH−3−Py]、[3821:2−CN−5−ACNH−3−Py]、[3822:4−CN−5−ACNH−3−Py]、[3823:6−CN−5−ACNH−3−Py]、[3824:2−OMe−5−ACNH−3−Py]、[3825:4−OMe−5−ACNH−3−Py]、[3826:6−OMe−5−ACNH−3−Py]、[3827:6−ACNH−3−Py]、[3828:2−Cl−6−ACNH−3−Py]、[3829:4−Cl−6−ACNH−3−Py]、[3830:5−Cl−6−ACNH−3−Py]、[3831:2−Me−6−ACNH−3−Py]、[3832:4−Me−6−ACNH−3−Py]、[3833:5−Me−6−ACNH−3−Py]、[3834:2−CF3−6−ACNH−3−Py]、[3835:4−CF3−6−ACNH−3−Py]、[3836:5−CF3−6−ACNH−3−Py]、[3837:2−CN−6−ACNH−3−Py]、[3838:4−CN−6−ACNH−3−Py]、[3839:5−CN−6−ACNH−3−Py]、[3840:2−OMe−6−ACNH−3−Py]、[3841:4−OMe−6−ACNH−3−Py]、[3842:5−OMe−6−ACNH−3−Py]、[3843:2−(N−AC−N−Me−N)−3−Py]、[3844:4−Cl−2−(N−AC−N−Me−N)−3−Py]、[3845:5−Cl−2−(N−AC−N−Me−N)−3−Py]、[3846:6−Cl−2−(N−AC−N−Me−N)−3−Py]、[3847:4−Me−2−(N−AC−N−Me−N)−3−Py]、[3848:5−Me−2−(N−AC−N−Me−N)−3−Py]、[3849:6−Me−2−(N−AC−N−Me−N)−3−Py]、[3850:4−CF3−2−(N−AC−N−Me−N)−3−Py]、[3851:5−CF3−2−(N−AC−N−Me−N)−3−Py]、[3852:6−CF3−2−(N−AC−N−Me−N)−3−Py]、[3853:4−CN−2−(N−AC−N−Me−N)−3−Py]、[3854:5−CN−2−(N−AC−N−Me−N)−3−Py]、[3855:6−CN−2−(N−AC−N−Me−N)−3−Py]、[3856:4−OMe−2−(N−AC−N−Me−N)−3−Py]、[3857:5−OMe−2−(N−AC−N−Me−N)−3−Py]、[3858:6−OMe−2−(N−AC−N−Me−N)−3−Py]、[3859:4−(N−AC−N−Me−N)−3−Py]、[3860:2−Cl−4−(N−AC−N−Me−N)−3−Py]、[3861:5−Cl−4−(N−AC−N−Me−N)−3−Py]、[3862:6−Cl−4−(N−AC−N−Me−N)−3−Py]、[3863:2−Me−4−(N−AC−N−Me−N)−3−Py]、[3864:5−Me−4−(N−AC−N−Me−N)−3−Py]、[3865:6−Me−4−(N−AC−N−Me−N)−3−Py]、[3866:2−CF3−4−(N−AC−N−Me−N)−3−Py]、[3867:5−CF3−4−(N−AC−N−Me−N)−3−Py]、[3868:6−CF3−4−(N−AC−N−Me−N)−3−Py]、[3869:2−CN−4−(N−AC−N−Me−N)−3−Py]、[3870:5−CN−4−(N−AC−N−Me−N)−3−Py]、[3871:6−CN−4−(N−AC−N−Me−N)−3−Py]、[3872:2−OMe−4−(N−AC−N−Me−N)−3−Py]、[3873:5−OMe−4−(N−AC−N−Me−N)−3−Py]、[3874:6−OMe−4−(N−AC−N−Me−N)−3−Py]、[3875:5−(N−AC−N−Me−N)−3−Py]、[3876:2−Cl−5−(N−AC−N−Me−N)−3−Py]、[3877:4−Cl−5−(N−AC−N−Me−N)−3−Py]、[3878:6−Cl−5−(N−AC−N−Me−N)−3−Py]、[3879:2−Me−5−(N−AC−N−Me−N)−3−Py]、[3880:4−Me−5−(N−AC−N−Me−N)−3−Py]、[3881:6−Me−5−(N−AC−N−Me−N)−3−Py]、[3882:2−CF3−5−(N−AC−N−Me−N)−3−Py]、[3883:4−CF3−5−(N−AC−N−Me−N)−3−Py]、[3884:6−CF3−5−(N−AC−N−Me−N)−3−Py]、[3885:2−CN−5−(N−AC−N−Me−N)−3−Py]、[3886:4−CN−5−(N−AC−N−Me−N)−3−Py]、[3887:6−CN−5−(N−AC−N−Me−N)−3−Py]、[3888:2−OMe−5−(N−AC−N−Me−N)−3−Py]、[3889:4−OMe−5−(N−AC−N−Me−N)−3−Py]、[3890:6−OMe−5−(N−AC−N−Me−N)−3−Py]、[3891:6−(N−AC−N−Me−N)−3−Py]、[3892:2−Cl−6−(N−AC−N−Me−N)−3−Py]、[3893:4−Cl−6−(N−AC−N−Me−N)−3−Py]、[3894:5−Cl−6−(N−AC−N−Me−N)−3−Py]、[3895:2−Me−6−(N−AC−N−Me−N)−3−Py]、[3896:4−Me−6−(N−AC−N−Me−N)−3−Py]、[3897:5−Me−6−(N−AC−N−Me−N)−3−Py]、[3898:2−CF3−6−(N−AC−N−Me−N)−3−Py]、[3899:4−CF3−6−(N−AC−N−Me−N)−3−Py]、[3900:5−CF3−6−(N−AC−N−Me−N)−3−Py]、 [3801: 6-Me-4-ACNH-3-Py], [3802: 2-CF3-4-ACNH-3-Py], [3803: 5-CF3-4-ACNH-3-Py], [3804 : 6-CF3-4-ACNH-3-Py], [3805: 2-CN-4-ACNH-3-Py], [3806: 5-CN-4-ACNH-3-Py], [3807: 6 -CN-4-ACNH-3-Py], [3808: 2-OMe-4-ACNH-3-Py], [3809: 5-OMe-4-ACNH-3-Py], [3810: 6-OMe -4-ACNH-3-Py], [3811: 5-ACNH-3-Py], [3812: 2-Cl-5-ACNH-3-Py], [3813: 4-Cl-5-ACNH-3 -Py], [3814: 6-Cl-5-ACNH-3- y], [3815: 2-Me-5-ACNH-3-Py], [3816: 4-Me-5-ACNH-3-Py], [3817: 6-Me-5-ACNH-3-Py] [3818: 2-CF3-5-ACNH-3-Py], [3819: 4-CF3-5-ACNH-3-Py], [3820: 6-CF3-5-ACNH-3-Py], [ 3821: 2-CN-5-ACNH-3-Py], [3822: 4-CN-5-ACNH-3-Py], [3823: 6-CN-5-ACNH-3-Py], [3824: 2-OMe-5-ACNH-3-Py], [3825: 4-OMe-5-ACNH-3-Py], [3826: 6-OMe-5-ACNH-3-Py], [3827: 6- ACNH-3-Py], [3828: 2-Cl-6-ACN -3-Py], [3829: 4-Cl-6-ACNH-3-Py], [3830: 5-Cl-6-ACNH-3-Py], [3831: 2-Me-6-ACNH-3 -Py], [3832: 4-Me-6-ACNH-3-Py], [3833: 5-Me-6-ACNH-3-Py], [3834: 2-CF3-6-ACNH-3-Py ], [3835: 4-CF3-6-ACNH-3-Py], [3836: 5-CF3-6-ACNH-3-Py], [3837: 2-CN-6-ACNH-3-Py], [3838: 4-CN-6-ACNH-3-Py], [3839: 5-CN-6-ACNH-3-Py], [3840: 2-OMe-6-ACNH-3-Py], [3841 : 4-OMe-6-ACNH-3-Py], [3842: 5-O Me-6-ACNH-3-Py], [3843: 2- (N-AC-N-Me-N) -3-Py], [3844: 4-Cl-2- (N-AC-N-Me). -N) -3-Py], [3845: 5-Cl-2- (N-AC-N-Me-N) -3-Py], [3846: 6-Cl-2- (N-AC-N). -Me-N) -3-Py], [3847: 4-Me-2- (N-AC-N-Me-N) -3-Py], [3848: 5-Me-2- (N-AC). -N-Me-N) -3-Py], [3849: 6-Me-2- (N-AC-N-Me-N) -3-Py], [3850: 4-CF3-2- (N -AC-N-Me-N) -3-Py], [3851: 5-CF3-2- (N-AC-N-Me-N) -3-Py], [3852: 6-CF3-2- (N-AC-N-M -N) -3-Py], [3853: 4-CN-2- (N-AC-N-Me-N) -3-Py], [3854: 5-CN-2- (N-AC-N). -Me-N) -3-Py], [3855: 6-CN-2- (N-AC-N-Me-N) -3-Py], [3856: 4-OMe-2- (N-AC) -N-Me-N) -3-Py], [3857: 5-OMe-2- (N-AC-N-Me-N) -3-Py], [3858: 6-OMe-2- (N -AC-N-Me-N) -3-Py], [3859: 4- (N-AC-N-Me-N) -3-Py], [3860: 2-Cl-4- (N-AC). -N-Me-N) -3-Py], [3861: 5-Cl-4- (N-AC-N-Me-N) -3-Py], [3862: 6-Cl-4- (N -AC-N-Me-N)- -Py], [3863: 2-Me-4- (N-AC-N-Me-N) -3-Py], [3864: 5-Me-4- (N-AC-N-Me-N). -3-Py], [3865: 6-Me-4- (N-AC-N-Me-N) -3-Py], [3866: 2-CF3-4- (N-AC-N-Me- N) -3-Py], [3867: 5-CF3-4- (N-AC-N-Me-N) -3-Py], [3868: 6-CF3-4- (N-AC-N- Me-N) -3-Py], [3869: 2-CN-4- (N-AC-N-Me-N) -3-Py], [3870: 5-CN-4- (N-AC- N-Me-N) -3-Py], [3871: 6-CN-4- (N-AC-N-Me-N) -3-Py], [3872: 2-OMe-4- (N- AC-N-Me-N)- 3-Py], [3873: 5-OMe-4- (N-AC-N-Me-N) -3-Py], [3874: 6-OMe-4- (N-AC-N-Me-N) ) -3-Py], [3875: 5- (N-AC-N-Me-N) -3-Py], [3876: 2-Cl-5- (N-AC-N-Me-N)- 3-Py], [3877: 4-Cl-5- (N-AC-N-Me-N) -3-Py], [3878: 6-Cl-5- (N-AC-N-Me-N) ) -3-Py], [3879: 2-Me-5- (N-AC-N-Me-N) -3-Py], [3880: 4-Me-5- (N-AC-N-Me). -N) -3-Py], [3881: 6-Me-5- (N-AC-N-Me-N) -3-Py], [3882: 2-CF3-5- (N-AC-N). -Me-N) -3-Py] [3883: 4-CF3-5- (N-AC-N-Me-N) -3-Py], [3884: 6-CF3-5- (N-AC-N-Me-N) -3-Py ], [3885: 2-CN-5- (N-AC-N-Me-N) -3-Py], [3886: 4-CN-5- (N-AC-N-Me-N) -3. -Py], [3887: 6-CN-5- (N-AC-N-Me-N) -3-Py], [3888: 2-OMe-5- (N-AC-N-Me-N) -3-Py], [3889: 4-OMe-5- (N-AC-N-Me-N) -3-Py], [3890: 6-OMe-5- (N-AC-N-Me- N) -3-Py], [3891: 6- (N-AC-N-Me-N) -3-Py], [3892: 2-Cl-6- (N-AC-N-Me-N) -3-Py], [3 93: 4-Cl-6- (N-AC-N-Me-N) -3-Py], [3894: 5-Cl-6- (N-AC-N-Me-N) -3-Py] [3895: 2-Me-6- (N-AC-N-Me-N) -3-Py], [3896: 4-Me-6- (N-AC-N-Me-N) -3-. Py], [3897: 5-Me-6- (N-AC-N-Me-N) -3-Py], [3898: 2-CF3-6- (N-AC-N-Me-N)- 3-Py], [3899: 4-CF3-6- (N-AC-N-Me-N) -3-Py], [3900: 5-CF3-6- (N-AC-N-Me-N) ) -3-Py],
[3901:2−CN−6−(N−AC−N−Me−N)−3−Py]、[3902:4−CN−6−(N−AC−N−Me−N)−3−Py]、[3903:5−CN−6−(N−AC−N−Me−N)−3−Py]、[3904:2−OMe−6−(N−AC−N−Me−N)−3−Py]、[3905:4−OMe−6−(N−AC−N−Me−N)−3−Py]、[3906:5−OMe−6−(N−AC−N−Me−N)−3−Py][3907:2−AC−3−Py]、[3908:4−Cl−2−AC−3−Py]、[3909:5−Cl−2−AC−3−Py]、[3910:6−Cl−2−AC−3−Py]、[3911:4−Me−2−AC−3−Py]、[3912:5−Me−2−AC−3−Py]、[3913:6−Me−2−AC−3−Py]、[3914:4−CF3−2−AC−3−Py]、[3915:5−CF3−2−AC−3−Py]、[3916:6−CF3−2−AC−3−Py]、[3917:4−CN−2−AC−3−Py]、[3918:5−CN−2−AC−3−Py]、[3919:6−CN−2−AC−3−Py]、[3920:4−OMe−2−AC−3−Py]、[3921:5−OMe−2−AC−3−Py]、[3922:6−OMe−2−AC−3−Py]、[3923:4−AC−3−Py]、[3924:2−Cl−4−AC−3−Py]、[3925:5−Cl−4−AC−3−Py]、[3926:6−Cl−4−AC−3−Py]、[3927:2−Me−4−AC−3−Py]、[3928:5−Me−4−AC−3−Py]、[3929:6−Me−4−AC−3−Py]、[3930:2−CF3−4−AC−3−Py]、[3931:5−CF3−4−AC−3−Py]、[3932:6−CF3−4−AC−3−Py]、[3933:2−CN−4−AC−3−Py]、[3934:5−CN−4−AC−3−Py]、[3935:6−CN−4−AC−3−Py]、[3936:2−OMe−4−AC−3−Py]、[3937:5−OMe−4−AC−3−Py]、[3938:6−OMe−4−AC−3−Py]、[3939:5−AC−3−Py]、[3940:2−Cl−5−AC−3−Py]、[3941:4−Cl−5−AC−3−Py]、[3942:6−Cl−5−AC−3−Py]、[3943:2−Me−5−AC−3−Py]、[3944:4−Me−5−AC−3−Py]、[3945:6−Me−5−AC−3−Py]、[3946:2−CF3−5−AC−3−Py]、[3947:4−CF3−5−AC−3−Py]、[3948:6−CF3−5−AC−3−Py]、[3949:2−CN−5−AC−3−Py]、[3950:4−CN−5−AC−3−Py]、[3951:6−CN−5−AC−3−Py]、[3952:2−OMe−5−AC−3−Py]、[3953:4−OMe−5−AC−3−Py]、[3954:6−OMe−5−AC−3−Py]、[3955:6−AC−3−Py]、[3956:2−Cl−6−AC−3−Py]、[3957:4−Cl−6−AC−3−Py]、[3958:5−Cl−6−AC−3−Py]、[3959:2−Me−6−AC−3−Py]、[3960:4−Me−6−AC−3−Py]、[3961:5−Me−6−AC−3−Py]、[3962:2−CF3−6−AC−3−Py]、[3963:4−CF3−6−AC−3−Py]、[3964:5−CF3−6−AC−3−Py]、[3965:2−CN−6−AC−3−Py]、[3966:4−CN−6−AC−3−Py]、[3967:5−CN−6−AC−3−Py]、[3968:2−OMe−6−AC−3−Py]、[3969:4−OMe−6−AC−3−Py]、[3970:5−OMe−6−AC−3−Py]、[3971:4−Py]、[3972:3−F−4−Py]、[3973:2−Cl−3−F−4−Py]、[3974:5−Cl−3−F−4−Py]、[3975:6−Cl−3−F−4−Py]、[3976:2−Me−3−F−4−Py]、[3977:5−Me−3−F−4−Py]、[3978:6−Me−3−F−4−Py]、[3979:2−CF3−3−F−4−Py]、[3980:5−CF3−3−F−4−Py]、[3981:6−CF3−3−F−4−Py]、[3982:2−CN−3−F−4−Py]、[3983:5−CN−3−F−4−Py]、[3984:6−CN−3−F−4−Py]、[3985:2−OMe−3−F−4−Py]、[3986:5−OMe−3−F−4−Py]、[3987:6−OMe−3−F−4−Py]、[3988:2−F−4−Py]、[3989:3−Cl−2−F−4−Py]、[3990:5−Cl−2−F−4−Py]、[3991:6−Cl−2−F−4−Py]、[3992:3−Me−2−F−4−Py]、[3993:5−Me−2−F−4−Py]、[3994:6−Me−2−F−4−Py]、[3995:3−CF3−2−F−4−Py]、[3996:5−CF3−2−F−4−Py]、[3997:6−CF3−2−F−4−Py]、[3998:3−CN−2−F−4−Py]、[3999:5−CN−2−F−4−Py]、[4000:6−CN−2−F−4−Py]、 [3901: 2-CN-6- (N-AC-N-Me-N) -3-Py], [3902: 4-CN-6- (N-AC-N-Me-N) -3-Py ], [3903: 5-CN-6- (N-AC-N-Me-N) -3-Py], [3904: 2-OMe-6- (N-AC-N-Me-N) -3. -Py], [3905: 4-OMe-6- (N-AC-N-Me-N) -3-Py], [3906: 5-OMe-6- (N-AC-N-Me-N) -3-Py] [3907: 2-AC-3-Py], [3908: 4-Cl-2-AC-3-Py], [3909: 5-Cl-2-AC-3-Py], [ 3910: 6-Cl-2-AC-3-Py], [3911: 4-Me-2-AC-3-Py], [3912: 5-Me-2-AC-3-Py], [3913: -Me-2-AC-3-Py], [3914: 4-CF3-2-AC-3-Py], [3915: 5-CF3-2-AC-3-Py], [3916: 6-CF3 -2-AC-3-Py], [3917: 4-CN-2-AC-3-Py], [3918: 5-CN-2-AC-3-Py], [3919: 6-CN-2 -AC-3-Py], [3920: 4-OMe-2-AC-3-Py], [3921: 5-OMe-2-AC-3-Py], [3922: 6-OMe-2-AC -3-Py], [3923: 4-AC-3-Py], [3924: 2-Cl-4-AC-3-Py], [3925: 5-Cl-4-AC-3-Py], [3926: 6-Cl-4-AC-3-Py], [3927: 2-Me-4-AC-3-Py], [3928: 5- e-4-AC-3-Py], [3929: 6-Me-4-AC-3-Py], [3930: 2-CF3-4-AC-3-Py], [3931: 5-CF3- 4-AC-3-Py], [3932: 6-CF3-4-AC-3-Py], [3933: 2-CN-4-AC-3-Py], [3934: 5-CN-4-. AC-3-Py], [3935: 6-CN-4-AC-3-Py], [3936: 2-OMe-4-AC-3-Py], [3937: 5-OMe-4-AC- 3-Py], [3938: 6-OMe-4-AC-3-Py], [3939: 5-AC-3-Py], [3940: 2-Cl-5-AC-3-Py], [ 3941: 4-Cl-5-AC-3-Py], [3942: 6-Cl-5-AC-3-Py], [3943: 2-Me- 5-AC-3-Py], [3944: 4-Me-5-AC-3-Py], [3945: 6-Me-5-AC-3-Py], [3946: 2-CF3-5 AC-3-Py], [3947: 4-CF3-5-AC-3-Py], [3948: 6-CF3-5-AC-3-Py], [3949: 2-CN-5-AC- 3-Py], [3950: 4-CN-5-AC-3-Py], [3951: 6-CN-5-AC-3-Py], [3952: 2-OMe-5-AC-3- Py], [3953: 4-OMe-5-AC-3-Py], [3954: 6-OMe-5-AC-3-Py], [3955: 6-AC-3-Py], [3956: 2-Cl-6-AC-3-Py], [3957: 4-Cl-6-AC-3-Py], [3958: 5-Cl-6 C-3-Py], [3959: 2-Me-6-AC-3-Py], [3960: 4-Me-6-AC-3-Py], [3961: 5-Me-6-AC- 3-Py], [3962: 2-CF3-6-AC-3-Py], [3963: 4-CF3-6-AC-3-Py], [3964: 5-CF3-6-AC-3- Py], [3965: 2-CN-6-AC-3-Py], [3966: 4-CN-6-AC-3-Py], [3967: 5-CN-6-AC-3-Py] [3968: 2-OMe-6-AC-3-Py], [3969: 4-OMe-6-AC-3-Py], [3970: 5-OMe-6-AC-3-Py], [ 3971: 4-Py], [3972: 3-F-4-Py], [3953: 2-Cl-3-F-4-Py], [3974] 5-Cl-3-F-4-Py], [3975: 6-Cl-3-F-4-Py], [3976: 2-Me-3-F-4-Py], [3777: 5- Me-3-F-4-Py], [3978: 6-Me-3-F-4-Py], [31979: 2-CF3-3-F-4-Py], [3980: 5-CF3- 3-F-4-Py], [3981: 6-CF3-3-3-F-4-Py], [3982: 2-CN-3-F-4-Py], [3983: 5-CN-3- F-4-Py], [3984: 6-CN-3-F-4-Py], [3985: 2-OMe-3-F-4-Py], [3986: 5-OMe-3-F- 4-Py], [3987: 6-OMe-3-F-4-Py], [3988: 2-F-4-Py], [3989: 3-Cl-2-F-4-Py], [ 3 990: 5-Cl-2-F-4-Py], [3991: 6-Cl-2-F-4-Py], [3992: 3-Me-2-F-4-Py], [3993: 5-Me-2-F-4-Py], [3994: 6-Me-2-F-4-Py], [3395: 3-CF3-2-F-4-Py], [3996: 5- CF3-2-F-4-Py], [3997: 6-CF3-2-F-4-Py], [3998: 3-CN-2-F-4-Py], [3999: 5-CN- 2-F-4-Py], [4000: 6-CN-2-F-4-Py],
[4001:3−OMe−2−F−4−Py]、[4002:5−OMe−2−F−4−Py]、[4003:6−OMe−2−F−4−Py]、[4004:5−F−4−Py]、[4005:3−Cl−5−F−4−Py]、[4006:2−Cl−5−F−4−Py]、[4007:6−Cl−5−F−4−Py]、[4008:3−Me−5−F−4−Py]、[4009:2−Me−5−F−4−Py]、[4010:6−Me−5−F−4−Py]、[4011:3−CF3−5−F−4−Py]、[4012:2−CF3−5−F−4−Py]、[4013:6−CF3−5−F−4−Py]、[4014:3−CN−5−F−4−Py]、[4015:2−CN−5−F−4−Py]、[4016:6−CN−5−F−4−Py]、[4017:3−OMe−5−F−4−Py]、[4018:2−OMe−5−F−4−Py]、[4019:6−OMe−5−F−4−Py]、[4020:6−F−4−Py]、[4021:3−Cl−6−F−4−Py]、[4022:2−Cl−6−F−4−Py]、[4023:5−Cl−6−F−4−Py]、[4024:3−Me−6−F−4−Py]、[4025:2−Me−6−F−4−Py]、[4026:5−Me−6−F−4−Py]、[4027:3−CF3−6−F−4−Py]、[4028:2−CF3−6−F−4−Py]、[4029:5−CF3−6−F−4−Py]、[4030:3−CN−6−F−4−Py]、[4031:2−CN−6−F−4−Py]、[4032:5−CN−6−F−4−Py]、[4033:3−OMe−6−F−4−Py]、[4034:2−OMe−6−F−4−Py]、[4035:5−OMe−6−F−4−Py]、[4036:3−Cl−4−Py]、[4037:2−Cl−3−Cl−4−Py]、[4038:5−Cl−3−Cl−4−Py]、[4039:6−Cl−3−Cl−4−Py]、[4040:2−Me−3−Cl−4−Py]、[4041:5−Me−3−Cl−4−Py]、[4042:6−Me−3−Cl−4−Py]、[4043:2−CF3−3−Cl−4−Py]、[4044:5−CF3−3−Cl−4−Py]、[4045:6−CF3−3−Cl−4−Py]、[4046:2−CN−3−Cl−4−Py]、[4047:5−CN−3−Cl−4−Py]、[4048:6−CN−3−Cl−4−Py]、[4049:2−OMe−3−Cl−4−Py]、[4050:5−OMe−3−Cl−4−Py]、[4051:6−OMe−3−Cl−4−Py]、[4052:2−Cl−4−Py]、[4053:3−Cl−2−Cl−4−Py]、[4054:5−Cl−2−Cl−4−Py]、[4055:6−Cl−2−Cl−4−Py]、[4056:3−Me−2−Cl−4−Py]、[4057:5−Me−2−Cl−4−Py]、[4058:6−Me−2−Cl−4−Py]、[4059:3−CF3−2−Cl−4−Py]、[4060:5−CF3−2−Cl−4−Py]、[4061:6−CF3−2−Cl−4−Py]、[4062:3−CN−2−Cl−4−Py]、[4063:5−CN−2−Cl−4−Py]、[4064:6−CN−2−Cl−4−Py]、[4065:3−OMe−2−Cl−4−Py]、[4066:5−OMe−2−Cl−4−Py]、[4067:6−OMe−2−Cl−4−Py]、[4068:5−Cl−4−Py]、[4069:2−Cl−5−Cl−4−Py]、[4070:5−Cl−5−Cl−4−Py]、[4071:6−Cl−5−Cl−4−Py]、[4072:2−Me−5−Cl−4−Py]、[4073:5−Me−5−Cl−4−Py]、[4074:6−Me−5−Cl−4−Py]、[4075:2−CF3−5−Cl−4−Py]、[4076:5−CF3−5−Cl−4−Py]、[4077:6−CF3−5−Cl−4−Py]、[4078:2−CN−5−Cl−4−Py]、[4079:3−CN−5−Cl−4−Py]、[4080:6−CN−5−Cl−4−Py]、[4081:2−OMe−5−Cl−4−Py]、[4082:5−OMe−5−Cl−4−Py]、[4083:6−OMe−5−Cl−4−Py]、[4084:6−Cl−4−Py]、[4085:3−Cl−6−Cl−4−Py]、[4086:2−Cl−6−Cl−4−Py]、[4087:5−Cl−6−Cl−4−Py]、[4088:3−Me−6−Cl−4−Py]、[4089:2−Me−6−Cl−4−Py]、[4090:5−Me−6−Cl−4−Py]、[4091:3−CF3−6−Cl−4−Py]、[4092:2−CF3−6−Cl−4−Py]、[4093:5−CF3−6−Cl−4−Py]、[4094:3−CN−6−Cl−4−Py]、[4095:2−CN−6−Cl−4−Py]、[4096:5−CN−6−Cl−4−Py]、[4097:3−OMe−6−Cl−4−Py]、[4098:2−OMe−6−Cl−4−Py]、[4099:5−OMe−6−Cl−4−Py]、[4100:3−Br−4−Py]、 [4001: 3-OMe-2-F-4-Py], [4002: 5-OMe-2-F-4-Py], [4003: 6-OMe-2-F-4-Py], [4004 : 5-F-4-Py], [4005: 3-Cl-5-F-4-Py], [4006: 2-Cl-5-F-4-Py], [4007: 6-Cl-5. -F-4-Py], [4008: 3-Me-5-F-4-Py], [4009: 2-Me-5-F-4-Py], [4010: 6-Me-5-F. -4-Py], [4011: 3-CF3-5-F-4-Py], [4012: 2-CF3-5-F-4-Py], [4013: 6-CF3-5-F-4] -Py], [4014: 3-CN-5-F-4-Py], [4015: 2-CN-5-F-4-Py], [4016: 6-CN-5-F-4- y], [4017: 3-OMe-5-F-4-Py], [4018: 2-OMe-5-F-4-Py], [4019: 6-OMe-5-F-4-Py] [4020: 6-F-4-Py], [4021: 3-Cl-6-F-4-Py], [4022: 2-Cl-6-F-4-Py], [4023: 5- Cl-6-F-4-Py], [4024: 3-Me-6-F-4-Py], [4025: 2-Me-6-F-4-Py], [4026: 5-Me- 6-F-4-Py], [4027: 3-CF3-6-F-4-Py], [4028: 2-CF3-6-F-4-Py], [4029: 5-CF3-6 F-4-Py], [4030: 3-CN-6-F-4-Py], [4031: 2-CN-6-F-4-Py], [4032: 5-CN-6 -4-Py], [4033: 3-OMe-6-F-4-Py], [4034: 2-OMe-6-F-4-Py], [4035: 5-OMe-6-F-4 -Py], [4036: 3-Cl-4-Py], [4037: 2-Cl-3-Cl-4-Py], [4038: 5-Cl-3-Cl-4-Py], [4039 : 6-Cl-3-Cl-4-Py], [4040: 2-Me-3-Cl-4-Py], [4041: 5-Me-3-Cl-4-Py], [4042: 6 -Me-3-Cl-4-Py], [4043: 2-CF3-3-Cl-4-Py], [4044: 5-CF3-3-Cl-4-Py], [4045: 6-CF3 -3-Cl-4-Py], [4046: 2-CN-3-Cl-4-Py], [4047: 5-CN-3-Cl-4-Py] ], [4048: 6-CN-3-Cl-4-Py], [4049: 2-OMe-3-Cl-4-Py], [4050: 5-OMe-3-Cl-4-Py], [4051: 6-OMe-3-Cl-4-Py], [4052: 2-Cl-4-Py], [4053: 3-Cl-2-Cl-4-Py], [4054: 5-Cl -2-Cl-4-Py], [4055: 6-Cl-2-Cl-4-Py], [4056: 3-Me-2-Cl-4-Py], [4057: 5-Me-2 -Cl-4-Py], [4058: 6-Me-2-Cl-4-Py], [4059: 3-CF3-2-Cl-4-Py], [4060: 5-CF3-2-Cl] -4-Py], [4061: 6-CF3-2-Cl-4-Py], [4062: 3-CN-2-Cl-4-Py], 4063: 5-CN-2-Cl-4-Py], [4064: 6-CN-2-Cl-4-Py], [4065: 3-OMe-2-Cl-4-Py], [4066: 5-OMe-2-Cl-4-Py], [4067: 6-OMe-2-Cl-4-Py], [4068: 5-Cl-4-Py], [4069: 2-Cl-5 Cl-4-Py], [4070: 5-Cl-5-Cl-4-Py], [4071: 6-Cl-5-Cl-4-Py], [4072: 2-Me-5-Cl- 4-Py], [4073: 5-Me-5-Cl-4-Py], [4074: 6-Me-5-Cl-4-Py], [4075: 2-CF3-5-Cl-4- Py], [4076: 5-CF3-5-Cl-4-Py], [4077: 6-CF3-5-Cl-4-Py], [4 78: 2-CN-5-Cl-4-Py], [4079: 3-CN-5-Cl-4-Py], [4080: 6-CN-5-Cl-4-Py], [4081: 2-OMe-5-Cl-4-Py], [4082: 5-OMe-5-Cl-4-Py], [4083: 6-OMe-5-Cl-4-Py], [4084: 6- Cl-4-Py], [4085: 3-Cl-6-Cl-4-Py], [4086: 2-Cl-6-Cl-4-Py], [4087: 5-Cl-6-Cl- 4-Py], [4088: 3-Me-6-Cl-4-Py], [4089: 2-Me-6-Cl-4-Py], [4090: 5-Me-6-Cl-4- Py], [4091: 3-CF3-6-Cl-4-Py], [4092: 2-CF3-6-Cl-4-Py], [4093: 5-CF3-6-Cl-4-Py], [4094: 3-CN-6-Cl-4-Py], [4095: 2-CN-6-Cl-4-Py], [4096: 5- CN-6-Cl-4-Py], [4097: 3-OMe-6-Cl-4-Py], [4098: 2-OMe-6-Cl-4-Py], [4099: 5-OMe- 6-Cl-4-Py], [4100: 3-Br-4-Py],
[4101:2−Cl−3−Br−4−Py]、[4102:5−Cl−3−Br−4−Py]、[4103:6−Cl−3−Br−4−Py]、[4104:2−Me−3−Br−4−Py]、[4105:5−Me−3−Br−4−Py]、[4106:6−Me−3−Br−4−Py]、[4107:2−CF3−3−Br−4−Py]、[4108:5−CF3−3−Br−4−Py]、[4109:6−CF3−3−Br−4−Py]、[4110:2−CN−3−Br−4−Py]、[4111:5−CN−3−Br−4−Py]、[4112:6−CN−3−Br−4−Py]、[4113:2−OMe−3−Br−4−Py]、[4114:5−OMe−3−Br−4−Py]、[4115:6−OMe−3−Br−4−Py]、[4116:2−Br−4−Py]、[4117:3−Cl−2−Br−4−Py]、[4118:5−Cl−2−Br−4−Py]、[4119:6−Cl−2−Br−4−Py]、[4120:3−Me−2−Br−4−Py]、[4121:5−Me−2−Br−4−Py]、[4122:6−Me−2−Br−4−Py]、[4123:3−CF3−2−Br−4−Py]、[4124:5−CF3−2−Br−4−Py]、[4125:6−CF3−2−Br−4−Py]、[4126:3−CN−2−Br−4−Py]、[4127:5−CN−2−Br−4−Py]、[4128:6−CN−2−Br−4−Py]、[4129:3−OMe−2−Br−4−Py]、[4130:5−OMe−2−Br−4−Py]、[4131:6−OMe−2−Br−4−Py]、[4132:5−Br−4−Py]、[4133:3−Cl−5−Br−4−Py]、[4134:2−Cl−5−Br−4−Py]、[4135:6−Cl−5−Br−4−Py]、[4136:3−Me−5−Br−4−Py]、[4137:2−Me−5−Br−4−Py]、[4138:6−Me−5−Br−4−Py]、[4139:3−CF3−5−Br−4−Py]、[4140:2−CF3−5−Br−4−Py]、[4141:6−CF3−5−Br−4−Py]、[4142:3−CN−5−Br−4−Py]、[4143:2−CN−5−Br−4−Py]、[4144:6−CN−5−Br−4−Py]、[4145:3−OMe−5−Br−4−Py]、[4146:2−OMe−5−Br−4−Py]、[4147:6−OMe−5−Br−4−Py]、[4148:6−Br−4−Py]、[4149:3−Cl−6−Br−4−Py]、[4150:2−Cl−6−Br−4−Py]、[4151:5−Cl−6−Br−4−Py]、[4152:3−Me−6−Br−4−Py]、[4153:2−Me−6−Br−4−Py]、[4154:5−Me−6−Br−4−Py]、[4155:3−CF3−6−Br−4−Py]、[4156:2−CF3−6−Br−4−Py]、[4157:5−CF3−6−Br−4−Py]、[4158:3−CN−6−Br−4−Py]、[4159:2−CN−6−Br−4−Py]、[4160:5−CN−6−Br−4−Py]、[4161:3−OMe−6−Br−4−Py]、[4162:2−OMe−6−Br−4−Py]、[4163:5−OMe−6−Br−4−Py]、[4164:3−I−4−Py]、[4165:2−Cl−3−I−4−Py]、[4166:5−Cl−3−I−4−Py]、[4167:6−Cl−3−I−4−Py]、[4168:2−Me−3−I−4−Py]、[4169:5−Me−3−I−4−Py]、[4170:6−Me−3−I−4−Py]、[4171:2−CF3−3−I−4−Py]、[4172:5−CF3−3−I−4−Py]、[4173:6−CF3−3−I−4−Py]、[4174:2−CN−3−I−4−Py]、[4175:5−CN−3−I−4−Py]、[4176:6−CN−3−I−4−Py]、[4177:2−OMe−3−I−4−Py]、[4178:5−OMe−3−I−4−Py]、[4179:6−OMe−3−I−4−Py]、[4180:2−I−4−Py]、[4181:3−Cl−2−I−4−Py]、[4182:5−Cl−2−I−4−Py]、[4183:6−Cl−2−I−4−Py]、[4184:3−Me−2−I−4−Py]、[4185:5−Me−2−I−4−Py]、[4186:6−Me−2−I−4−Py]、[4187:3−CF3−2−I−4−Py]、[4188:5−CF3−2−I−4−Py]、[4189:6−CF3−2−I−4−Py]、[4190:3−CN−2−I−4−Py]、[4191:5−CN−2−I−4−Py]、[4192:6−CN−2−I−4−Py]、[4193:3−OMe−2−I−4−Py]、[4194:5−OMe−2−I−4−Py]、[4195:6−OMe−2−I−4−Py]、[4196:5−I−4−Py]、[4197:3−Cl−5−I−4−Py]、[4198:2−Cl−5−I−4−Py]、[4199:6−Cl−5−I−4−Py]、[4200:3−Me−5−I−4−Py]、 [4101: 2-Cl-3-Br-4-Py], [4102: 5-Cl-3-Br-4-Py], [4103: 6-Cl-3-Br-4-Py], [4104 : 2-Me-3-Br-4-Py], [4105: 5-Me-3-Br-4-Py], [4106: 6-Me-3-Br-4-Py], [4107: 2 -CF3-3-Br-4-Py], [4108: 5-CF3-3-Br-4-Py], [4109: 6-CF3-3-Br-4-Py], [4110: 2-CN -3-Br-4-Py], [4111: 5-CN-3-Br-4-Py], [4112: 6-CN-3-Br-4-Py], [4113: 2-OMe-3 -Br-4-Py], [4114: 5-OMe-3-Br-4-Py], [4115: 6-OMe-3-Br-4-P ], [4116: 2-Br-4-Py], [4117: 3-Cl-2-Br-4-Py], [4118: 5-Cl-2-Br-4-Py], [4119: 6 -Cl-2-Br-4-Py], [4120: 3-Me-2-Br-4-Py], [4121: 5-Me-2-Br-4-Py], [4122: 6-Me -2-Br-4-Py], [4123: 3-CF3-2-Br-4-Py], [4124: 5-CF3-2-Br-4-Py], [4125: 6-CF3-2 -Br-4-Py], [4126: 3-CN-2-Br-4-Py], [4127: 5-CN-2-Br-4-Py], [4128: 6-CN-2-Br -4-Py], [4129: 3-OMe-2-Br-4-Py], [4130: 5-OMe-2-Br-4-Py], 4131: 6-OMe-2-Br-4-Py], [4132: 5-Br-4-Py], [4133: 3-Cl-5-Br-4-Py], [4134: 2-Cl- 5-Br-4-Py], [4135: 6-Cl-5-Br-4-Py], [4136: 3-Me-5-Br-4-Py], [4137: 2-Me-5- Br-4-Py], [4138: 6-Me-5-Br-4-Py], [4139: 3-CF3-5-Br-4-Py], [4140: 2-CF3-5-Br- 4-Py], [4141: 6-CF3-5-Br-4-Py], [4142: 3-CN-5-Br-4-Py], [4143: 2-CN-5-Br-4- Py], [4144: 6-CN-5-Br-4-Py], [4145: 3-OMe-5-Br-4-Py], [414 6: 2-OMe-5-Br-4-Py], [4147: 6-OMe-5-Br-4-Py], [4148: 6-Br-4-Py], [4149: 3-Cl- 6-Br-4-Py], [4150: 2-Cl-6-Br-4-Py], [4151: 5-Cl-6-Br-4-Py], [4152: 3-Me-6- Br-4-Py], [4153: 2-Me-6-Br-4-Py], [4154: 5-Me-6-Br-4-Py], [4155: 3-CF3-6-Br- 4-Py], [4156: 2-CF3-6-Br-4-Py], [4157: 5-CF3-6-Br-4-Py], [4158: 3-CN-6-Br-4- Py], [4159: 2-CN-6-Br-4-Py], [4160: 5-CN-6-Br-4-Py], [4161: 3 OMe-6-Br-4-Py], [4162: 2-OMe-6-Br-4-Py], [4163: 5-OMe-6-Br-4-Py], [4164: 3-I- 4-Py], [4165: 2-Cl-3-I-4-Py], [4166: 5-Cl-3-I-4-Py], [4167: 6-Cl-3-I-4- Py], [4168: 2-Me-3-I-4-Py], [4169: 5-Me-3-I-4-Py], [4170: 6-Me-3-I-4-Py] [4171: 2-CF3-3-1-I-4-Py], [4172: 5-CF3-3-3-I-4-Py], [4173: 6-CF3-3-3-I-4-Py], [ 4174: 2-CN-3-I-4-Py], [4175: 5-CN-3-I-4-Py], [4176: 6-CN-3-I-4-Py], 4177: 2-OMe-3-I-4-Py], [4178: 5-OMe-3-I-4-Py], [4179: 6-OMe-3-I-4-Py], [4180: 2-I-4-Py], [4181: 3-Cl-2-I-4-Py], [4182: 5-Cl-2-I-4-Py], [4183: 6-Cl-2- I-4-Py], [4184: 3-Me-2-I-4-Py], [4185: 5-Me-2-I-4-Py], [4186: 6-Me-2-I- 4-Py], [4187: 3-CF3-2-I-4-Py], [4188: 5-CF3-2-I-4-Py], [4189: 6-CF3-2-I-4- Py], [4190: 3-CN-2-I-4-Py], [4191: 5-CN-2-I-4-Py], [4192: 6-CN-2-I-4-P y], [4193: 3-OMe-2-I-4-Py], [4194: 5-OMe-2-I-4-Py], [4195: 6-OMe-2-I-4-Py] [4196: 5-I-4-Py], [4197: 3-Cl-5-I-4-Py], [4198: 2-Cl-5-I-4-Py], [4199: 6- Cl-5-I-4-Py], [4200: 3-Me-5-I-4-Py],
[4201:2−Me−5−I−4−Py]、[4202:6−Me−5−I−4−Py]、[4203:3−CF3−5−I−4−Py]、[4204:2−CF3−5−I−4−Py]、[4205:6−CF3−5−I−4−Py]、[4206:3−CN−5−I−4−Py]、[4207:2−CN−5−I−4−Py]、[4208:6−CN−5−I−4−Py]、[4209:3−OMe−5−I−4−Py]、[4210:2−OMe−5−I−4−Py]、[4211:6−OMe−5−I−4−Py]、[4212:6−I−4−Py]、[4213:3−Cl−6−I−4−Py]、[4214:2−Cl−6−I−4−Py]、[4215:5−Cl−6−I−4−Py]、[4216:3−Me−6−I−4−Py]、[4217:2−Me−6−I−4−Py]、[4218:5−Me−6−I−4−Py]、[4219:3−CF3−6−I−4−Py]、[4220:2−CF3−6−I−4−Py]、[4221:5−CF3−6−I−4−Py]、[4222:3−CN−6−I−4−Py]、[4223:2−CN−6−I−4−Py]、[4224:5−CN−6−I−4−Py]、[4225:3−OMe−6−I−4−Py]、[4226:2−OMe−6−I−4−Py]、[4227:5−OMe−6−I−4−Py]、[4228:3−Me−4−Py]、[4229:2−Cl−3−Me−4−Py]、[4230:5−Cl−3−Me−4−Py]、[4231:6−Cl−3−Me−4−Py]、[4232:2−Me−3−Me−4−Py]、[4233:5−Me−3−Me−4−Py]、[4234:6−Me−3−Me−4−Py]、[4235:2−CF3−3−Me−4−Py]、[4236:5−CF3−3−Me−4−Py]、[4237:6−CF3−3−Me−4−Py]、[4238:2−CN−3−Me−4−Py]、[4239:5−CN−3−Me−4−Py]、[4240:6−CN−3−Me−4−Py]、[4241:2−OMe−3−Me−4−Py]、[4242:5−OMe−3−Me−4−Py]、[4243:6−OMe−3−Me−4−Py]、[4244:2−Me−4−Py]、[4245:3−Cl−2−Me−4−Py]、[4246:5−Cl−2−Me−4−Py]、[4247:6−Cl−2−Me−4−Py]、[4248:3−Me−2−Me−4−Py]、[4249:5−Me−2−Me−4−Py]、[4250:6−Me−2−Me−4−Py]、[4251:3−CF3−2−Me−4−Py]、[4252:5−CF3−2−Me−4−Py]、[4253:6−CF3−2−Me−4−Py]、[4254:3−CN−2−Me−4−Py]、[4255:5−CN−2−Me−4−Py]、[4256:6−CN−2−Me−4−Py]、[4257:3−OMe−2−Me−4−Py]、[4258:5−OMe−2−Me−4−Py]、[4259:6−OMe−2−Me−4−Py]、[4260:5−Me−4−Py]、[4261:3−Cl−5−Me−4−Py]、[4262:2−Cl−5−Me−4−Py]、[4263:6−Cl−5−Me−4−Py]、[4264:3−Me−5−Me−4−Py]、[4265:2−Me−5−Me−4−Py]、[4266:6−Me−5−Me−4−Py]、[4267:3−CF3−5−Me−4−Py]、[4268:2−CF3−5−Me−4−Py]、[4269:6−CF3−5−Me−4−Py]、[4270:3−CN−5−Me−4−Py]、[4271:2−CN−5−Me−4−Py]、[4272:6−CN−5−Me−4−Py]、[4273:3−OMe−5−Me−4−Py]、[4274:2−OMe−5−Me−4−Py]、[4275:6−OMe−5−Me−4−Py]、[4276:6−Me−4−Py]、[4277:3−Cl−6−Me−4−Py]、[4278:2−Cl−6−Me−4−Py]、[4279:5−Cl−6−Me−4−Py]、[4280:3−Me−6−Me−4−Py]、[4281:2−Me−6−Me−4−Py]、[4282:5−Me−6−Me−4−Py]、[4283:3−CF3−6−Me−4−Py]、[4284:2−CF3−6−Me−4−Py]、[4285:5−CF3−6−Me−4−Py]、[4286:3−CN−6−Me−4−Py]、[4287:2−CN−6−Me−4−Py]、[4288:5−CN−6−Me−4−Py]、[4289:3−OMe−6−Me−4−Py]、[4290:2−OMe−6−Me−4−Py]、[4291:5−OMe−6−Me−4−Py]、[4292:3−OMe−4−Py]、[4293:2−Cl−3−OMe−4−Py]、[4294:5−Cl−3−OMe−4−Py]、[4295:6−Cl−3−OMe−4−Py]、[4296:2−Me−3−OMe−4−Py]、[4297:5−Me−3−OMe−4−Py]、[4298:6−Me−3−OMe−4−Py]、[4299:2−CF3−3−OMe−4−Py]、[4300:5−CF3−3−OMe−4−Py]、 [4201: 2-Me-5-I-4-Py], [4202: 6-Me-5-I-4-Py], [4203: 3-CF3-5-I-4-Py], [4204] : 2-CF3-5-I-4-Py], [4205: 6-CF3-5-I-4-Py], [4206: 3-CN-5-I-4-Py], [4207: 2 -CN-5-I-4-Py], [4208: 6-CN-5-I-4-Py], [4209: 3-OMe-5-I-4-Py], [4210: 2-OMe -5-I-4-Py], [4211: 6-OMe-5-I-4-Py], [4212: 6-I-4-Py], [4213: 3-Cl-6-I-4 -Py], [4214: 2-Cl-6-I-4-Py], [4215: 5-Cl-6-I-4-Py], [4216: 3-Me-6-I-4- y], [4217: 2-Me-6-I-4-Py], [4218: 5-Me-6-I-4-Py], [4219: 3-CF3-6-I-4-Py] [4220: 2-CF3-6-I-4-Py], [4221: 5-CF3-6-I-4-Py], [4222: 3-CN-6-I-4-Py], [ 4223: 2-CN-6-I-4-Py], [4224: 5-CN-6-I-4-Py], [4225: 3-OMe-6-I-4-Py], [4226: 2-OMe-6-I-4-Py], [4227: 5-OMe-6-I-4-Py], [4228: 3-Me-4-Py], [4229: 2-Cl-3- Me-4-Py], [4230: 5-Cl-3-Me-4-Py], [4231: 6-Cl-3-Me-4-Py], [4232: 2-M -3-Me-4-Py], [4233: 5-Me-3-Me-4-Py], [4234: 6-Me-3-Me-4-Py], [4235: 2-CF3-3. -Me-4-Py], [4236: 5-CF3-3-Me-4-Py], [4237: 6-CF3-3-Me-4-Py], [4238: 2-CN-3-Me. -4-Py], [4239: 5-CN-3-Me-4-Py], [4240: 6-CN-3-Me-4-Py], [4241: 2-OMe-3-Me-4 -Py], [4242: 5-OMe-3-Me-4-Py], [4243: 6-OMe-3-Me-4-Py], [4244: 2-Me-4-Py], [4245. : 3-Cl-2-Me-4-Py], [4246: 5-Cl-2-Me-4-Py], [4247: 6-Cl-2 -Me-4-Py], [4248: 3-Me-2-Me-4-Py], [4249: 5-Me-2-Me-4-Py], [4250: 6-Me-2-Me -4-Py], [4251: 3-CF3-2-Me-4-Py], [4252: 5-CF3-2-Me-4-Py], [4253: 6-CF3-2-Me-4. -Py], [4254: 3-CN-2-Me-4-Py], [4255: 5-CN-2-Me-4-Py], [4256: 6-CN-2-Me-4-Py ], [4257: 3-OMe-2-Me-4-Py], [4258: 5-OMe-2-Me-4-Py], [4259: 6-OMe-2-Me-4-Py], [4260: 5-Me-4-Py], [4261: 3-Cl-5-Me-4-Py], [4262: 2-Cl-5-M -4-Py], [4263: 6-Cl-5-Me-4-Py], [4264: 3-Me-5-Me-4-Py], [4265: 2-Me-5-Me-4. -Py], [4266: 6-Me-5-Me-4-Py], [4267: 3-CF3-5-Me-4-Py], [4268: 2-CF3-5-Me-4-Py]. ], [4269: 6-CF3-5-Me-4-Py], [4270: 3-CN-5-Me-4-Py], [4271: 2-CN-5-Me-4-Py], [4272: 6-CN-5-Me-4-Py], [4273: 3-OMe-5-Me-4-Py], [4274: 2-OMe-5-Me-4-Py], [4275 : 6-OMe-5-Me-4-Py], [4276: 6-Me-4-Py], [4277: 3-Cl-6-Me- -Py], [4278: 2-Cl-6-Me-4-Py], [4279: 5-Cl-6-Me-4-Py], [4280: 3-Me-6-Me-4-Py ], [4281: 2-Me-6-Me-4-Py], [4282: 5-Me-6-Me-4-Py], [4283: 3-CF3-6-Me-4-Py], [4284: 2-CF3-6-Me-4-Py], [4285: 5-CF3-6-Me-4-Py], [4286: 3-CN-6-Me-4-Py], [4287 : 2-CN-6-Me-4-Py], [4288: 5-CN-6-Me-4-Py], [4289: 3-OMe-6-Me-4-Py], [4290: 2 -OMe-6-Me-4-Py], [4291: 5-OMe-6-Me-4-Py], [4292: 3-OMe-4- Py], [4293: 2-Cl-3-OMe-4-Py], [4294: 5-Cl-3-OMe-4-Py], [4295: 6-Cl-3-OMe-4-Py] [4296: 2-Me-3-OMe-4-Py], [4297: 5-Me-3-OMe-4-Py], [4298: 6-Me-3-OMe-4-Py], [ 4299: 2-CF3-3-OMe-4-Py], [4300: 5-CF3-3-OMe-4-Py],
[4301:6−CF3−3−OMe−4−Py]、[4302:2−CN−3−OMe−4−Py]、[4303:5−CN−3−OMe−4−Py]、[4304:6−CN−3−OMe−4−Py]、[4305:2−OMe−3−OMe−4−Py]、[4306:5−OMe−3−OMe−4−Py]、[4307:6−OMe−3−OMe−4−Py]、[4308:2−OMe−4−Py]、[4309:3−Cl−2−OMe−4−Py]、[4310:5−Cl−2−OMe−4−Py]、[4311:6−Cl−2−OMe−4−Py]、[4312:3−Me−2−OMe−4−Py]、[4313:5−Me−2−OMe−4−Py]、[4314:6−Me−2−OMe−4−Py]、[4315:3−CF3−2−OMe−4−Py]、[4316:5−CF3−2−OMe−4−Py]、[4317:6−CF3−2−OMe−4−Py]、[4318:3−CN−2−OMe−4−Py]、[4319:5−CN−2−OMe−4−Py]、[4320:6−CN−2−OMe−4−Py]、[4321:3−OMe−2−OMe−4−Py]、[4322:5−OMe−2−OMe−4−Py]、[4323:6−OMe−2−OMe−4−Py]、[4324:5−OMe−4−Py]、[4325:3−Cl−5−OMe−4−Py]、[4326:2−Cl−5−OMe−4−Py]、[4327:6−Cl−5−OMe−4−Py]、[4328:3−Me−5−OMe−4−Py]、[4329:2−Me−5−OMe−4−Py]、[4330:6−Me−5−OMe−4−Py]、[4331:3−CF3−5−OMe−4−Py]、[4332:2−CF3−5−OMe−4−Py]、[4333:6−CF3−5−OMe−4−Py]、[4334:3−CN−5−OMe−4−Py]、[4335:2−CN−5−OMe−4−Py]、[4336:6−CN−5−OMe−4−Py]、[4337:3−OMe−5−OMe−4−Py]、[4338:2−OMe−5−OMe−4−Py]、[4339:6−OMe−5−OMe−4−Py]、[4340:6−OMe−4−Py]、[4341:3−Cl−6−OMe−4−Py]、[4342:2−Cl−6−OMe−4−Py]、[4343:5−Cl−6−OMe−4−Py]、[4344:3−Me−6−OMe−4−Py]、[4345:2−Me−6−OMe−4−Py]、[4346:5−Me−6−OMe−4−Py]、[4347:3−CF3−6−OMe−4−Py]、[4348:2−CF3−6−OMe−4−Py]、[4349:5−CF3−6−OMe−4−Py]、[4350:3−CN−6−OMe−4−Py]、[4351:2−CN−6−OMe−4−Py]、[4352:5−CN−6−OMe−4−Py]、[4353:3−OMe−6−OMe−4−Py]、[4354:2−OMe−6−OMe−4−Py]、[4355:5−OMe−6−OMe−4−Py]、[4356:3−CF3−4−Py]、[4357:2−Cl−3−CF3−4−Py]、[4358:5−Cl−3−CF3−4−Py]、[4359:6−Cl−3−CF3−4−Py]、[4360:2−Me−3−CF3−4−Py]、[4361:5−Me−3−CF3−4−Py]、[4362:6−Me−3−CF3−4−Py]、[4363:2−CF3−3−CF3−4−Py]、[4364:5−CF3−3−CF3−4−Py]、[4365:6−CF3−3−CF3−4−Py]、[4366:2−CN−3−CF3−4−Py]、[4367:5−CN−3−CF3−4−Py]、[4368:6−CN−3−CF3−4−Py]、[4369:2−OMe−3−CF3−4−Py]、[4370:5−OMe−3−CF3−4−Py]、[4371:6−OMe−3−CF3−4−Py]、[4372:2−CF3−4−Py]、[4373:3−Cl−2−CF3−4−Py]、[4374:5−Cl−2−CF3−4−Py]、[4375:6−Cl−2−CF3−4−Py]、[4376:3−Me−2−CF3−4−Py]、[4377:5−Me−2−CF3−4−Py]、[4378:6−Me−2−CF3−4−Py]、[4379:3−CF3−2−CF3−4−Py]、[4380:5−CF3−2−CF3−4−Py]、[4381:6−CF3−2−CF3−4−Py]、[4382:3−CN−2−CF3−4−Py]、[4383:5−CN−2−CF3−4−Py]、[4384:6−CN−2−CF3−4−Py]、[4385:3−OMe−2−CF3−4−Py]、[4386:5−OMe−2−CF3−4−Py]、[4387:6−OMe−2−CF3−4−Py]、[4388:5−CF3−4−Py]、[4389:3−Cl−5−CF3−4−Py]、[4390:2−Cl−5−CF3−4−Py]、[4391:6−Cl−5−CF3−4−Py]、[4392:3−Me−5−CF3−4−Py]、[4393:2−Me−5−CF3−4−Py]、[4394:6−Me−5−CF3−4−Py]、[4395:3−CF3−5−CF3−4−Py]、[4396:2−CF3−5−CF3−4−Py]、[4397:6−CF3−5−CF3−4−Py]、[4398:3−CN−5−CF3−4−Py]、[4399:2−CN−5−CF3−4−Py]、[4400:6−CN−5−CF3−4−Py]、 [4301: 6-CF3-3-OMe-4-Py], [4302: 2-CN-3-OMe-4-Py], [4303: 5-CN-3-OMe-4-Py], [4304 : 6-CN-3-OMe-4-Py], [4305: 2-OMe-3-OMe-4-Py], [4306: 5-OMe-3-OMe-4-Py], [4307: 6 -OMe-3-OMe-4-Py], [4308: 2-OMe-4-Py], [4309: 3-Cl-2-OMe-4-Py], [4310: 5-Cl-2-OMe -4-Py], [4311: 6-Cl-2-OMe-4-Py], [4312: 3-Me-2-OMe-4-Py], [4313: 5-Me-2-OMe-4 -Py], [4314: 6-Me-2-OMe-4-Py], [4315: 3-CF3- -OMe-4-Py], [4316: 5-CF3-2-OMe-4-Py], [4317: 6-CF3-2-OMe-4-Py], [4318: 3-CN-2-OMe -4-Py], [4319: 5-CN-2-OMe-4-Py], [4320: 6-CN-2-OMe-4-Py], [4321: 3-OMe-2-OMe-4 -Py], [4322: 5-OMe-2-OMe-4-Py], [4323: 6-OMe-2-OMe-4-Py], [4324: 5-OMe-4-Py], [4325. : 3-Cl-5-OMe-4-Py], [4326: 2-Cl-5-OMe-4-Py], [4327: 6-Cl-5-OMe-4-Py], [4328: 3 -Me-5-OMe-4-Py], [4329: 2-Me-5-OMe-4-Py] [4330: 6-Me-5-OMe-4-Py], [4331: 3-CF3-5-OMe-4-Py], [4332: 2-CF3-5-OMe-4-Py], [4333 : 6-CF3-5-OMe-4-Py], [4334: 3-CN-5-OMe-4-Py], [4335: 2-CN-5-OMe-4-Py], [4336: 6 -CN-5-OMe-4-Py], [4337: 3-OMe-5-OMe-4-Py], [4338: 2-OMe-5-OMe-4-Py], [4339: 6-OMe -5-OMe-4-Py], [4340: 6-OMe-4-Py], [4341: 3-Cl-6-OMe-4-Py], [4342: 2-Cl-6-OMe-4 -Py], [4343: 5-Cl-6-OMe-4-Py], [4344: 3-Me -6-OMe-4-Py], [4345: 2-Me-6-OMe-4-Py], [4346: 5-Me-6-OMe-4-Py], [4347: 3-CF3-6 -OMe-4-Py], [4348: 2-CF3-6-OMe-4-Py], [4349: 5-CF3-6-OMe-4-Py], [4350: 3-CN-6-OMe -4-Py], [4351: 2-CN-6-OMe-4-Py], [4352: 5-CN-6-OMe-4-Py], [4353: 3-OMe-6-OMe-4 -Py], [4354: 2-OMe-6-OMe-4-Py], [4355: 5-OMe-6-OMe-4-Py], [4356: 3-CF3-4-Py], [4357 : 2-Cl-3-CF3-4-Py], [4358: 5-Cl-3-CF3-4-P ], [4359: 6-Cl-3-CF3-4-Py], [4360: 2-Me-3-CF3-4-Py], [4361: 5-Me-3-CF3-4-Py], [4362: 6-Me-3-CF3-4-Py], [4363: 2-CF3-3-CF3-4-Py], [4364: 5-CF3-3-CF3-4-Py], [4365 : 6-CF3-3-CF3-4-Py], [4366: 2-CN-3-CF3-4-Py], [4367: 5-CN-3-CF3-4-Py], [4368: 6 -CN-3-CF3-4-Py], [4369: 2-OMe-3-CF3-4-Py], [4370: 5-OMe-3-CF3-4-Py], [4371: 6-OMe -3-CF3-4-Py], [4372: 2-CF3-4-Py], [4373: 3 Cl-2-CF3-4-Py], [4374: 5-Cl-2-CF3-4-Py], [4375: 6-Cl-2-CF3-4-Py], [4376: 3-Me- 2-CF3-4-Py], [4377: 5-Me-2-CF3-4-Py], [4378: 6-Me-2-CF3-4-Py], [4379: 3-CF3-2- CF3-4-Py], [4380: 5-CF3-2-CF3-4-Py], [4381: 6-CF3-2-CF3-4-Py], [4382: 3-CN-2-CF3- 4-Py], [4383: 5-CN-2-CF3-4-Py], [4384: 6-CN-2-CF3-4-Py], [4385: 3-OMe-2-CF3-4- Py], [4386: 5-OMe-2-CF3-4-Py], [4387: 6-OMe-2- CF3-4-Py], [4388: 5-CF3-4-Py], [4389: 3-Cl-5-CF3-4-Py], [4390: 2-Cl-5-CF3-4-Py] [4391: 6-Cl-5-CF3-4-Py], [4392: 3-Me-5-CF3-4-Py], [4393: 2-Me-5-CF3-4-Py], [ 4394: 6-Me-5-CF3-4-Py], [4395: 3-CF3-5-CF3-4-Py], [4396: 2-CF3-5-CF3-4-Py], [4397: 6-CF3-5-CF3-4-Py], [4398: 3-CN-5-CF3-4-Py], [4399: 2-CN-5-CF3-4-Py], [4400: 6- CN-5-CF3-4-Py],
[4401:3−OMe−5−CF3−4−Py]、[4402:2−OMe−5−CF3−4−Py]、[4403:6−OMe−5−CF3−4−Py]、[4404:6−CF3−4−Py]、[4405:3−Cl−6−CF3−4−Py]、[4406:2−Cl−6−CF3−4−Py]、[4407:5−Cl−6−CF3−4−Py]、[4408:3−Me−6−CF3−4−Py]、[4409:2−Me−6−CF3−4−Py]、[4410:5−Me−6−CF3−4−Py]、[4411:3−CF3−6−CF3−4−Py]、[4412:2−CF3−6−CF3−4−Py]、[4413:5−CF3−6−CF3−4−Py]、[4414:3−CN−6−CF3−4−Py]、[4415:2−CN−6−CF3−4−Py]、[4416:5−CN−6−CF3−4−Py]、[4417:3−OMe−6−CF3−4−Py]、[4418:2−OMe−6−CF3−4−Py]、[4419:5−OMe−6−CF3−4−Py]、[4420:3−OCF3−4−Py]、[4421:2−Cl−3−OCF3−4−Py]、[4422:5−Cl−3−OCF3−4−Py]、[4423:6−Cl−3−OCF3−4−Py]、[4424:2−Me−3−OCF3−4−Py]、[4425:5−Me−3−OCF3−4−Py]、[4426:6−Me−3−OCF3−4−Py]、[4427:2−CF3−3−OCF3−4−Py]、[4428:5−CF3−3−OCF3−4−Py]、[4429:6−CF3−3−OCF3−4−Py]、[4430:2−CN−3−OCF3−4−Py]、[4431:5−CN−3−OCF3−4−Py]、[4432:6−CN−3−OCF3−4−Py]、[4433:2−OMe−3−OCF3−4−Py]、[4434:5−OMe−3−OCF3−4−Py]、[4435:6−OMe−3−OCF3−4−Py]、[4436:2−OCF3−4−Py]、[4437:3−Cl−2−OCF3−4−Py]、[4438:5−Cl−2−OCF3−4−Py]、[4439:6−Cl−2−OCF3−4−Py]、[4440:3−Me−2−OCF3−4−Py]、[4441:5−Me−2−OCF3−4−Py]、[4442:6−Me−2−OCF3−4−Py]、[4443:3−CF3−2−OCF3−4−Py]、[4444:5−CF3−2−OCF3−4−Py]、[4445:6−CF3−2−OCF3−4−Py]、[4446:3−CN−2−OCF3−4−Py]、[4447:5−CN−2−OCF3−4−Py]、[4448:6−CN−2−OCF3−4−Py]、[4449:3−OMe−2−OCF3−4−Py]、[4450:5−OMe−2−OCF3−4−Py]、[4451:6−OMe−2−OCF3−4−Py]、[4452:5−OCF3−4−Py]、[4453:3−Cl−5−OCF3−4−Py]、[4454:2−Cl−5−OCF3−4−Py]、[4455:6−Cl−5−OCF3−4−Py]、[4456:3−Me−5−OCF3−4−Py]、[4457:2−Me−5−OCF3−4−Py]、[4458:6−Me−5−OCF3−4−Py]、[4459:3−CF3−5−OCF3−4−Py]、[4460:2−CF3−5−OCF3−4−Py]、[4461:6−CF3−5−OCF3−4−Py]、[4462:3−CN−5−OCF3−4−Py]、[4463:2−CN−5−OCF3−4−Py]、[4464:6−CN−5−OCF3−4−Py]、[4465:3−OMe−5−OCF3−4−Py]、[4466:2−OMe−5−OCF3−4−Py]、[4467:6−OMe−5−OCF3−4−Py]、[4468:6−OCF3−4−Py]、[4469:3−Cl−6−OCF3−4−Py]、[4470:2−Cl−6−OCF3−4−Py]、[4471:5−Cl−6−OCF3−4−Py]、[4472:3−Me−6−OCF3−4−Py]、[4473:2−Me−6−OCF3−4−Py]、[4474:5−Me−6−OCF3−4−Py]、[4475:3−CF3−6−OCF3−4−Py]、[4476:2−CF3−6−OCF3−4−Py]、[4477:5−CF3−6−OCF3−4−Py]、[4478:3−CN−6−OCF3−4−Py]、[4479:2−CN−6−OCF3−4−Py]、[4480:5−CN−6−OCF3−4−Py]、[4481:3−OMe−6−OCF3−4−Py]、[4482:2−OMe−6−OCF3−4−Py]、[4483:5−OMe−6−OCF3−4−Py]、[4484:3−CHF2−4−Py]、[4485:2−Cl−3−CHF2−4−Py]、[4486:5−Cl−3−CHF2−4−Py]、[4487:6−Cl−3−CHF2−4−Py]、[4488:2−Me−3−CHF2−4−Py]、[4489:5−Me−3−CHF2−4−Py]、[4490:6−Me−3−CHF2−4−Py]、[4491:2−CF3−3−CHF2−4−Py]、[4492:5−CF3−3−CHF2−4−Py]、[4493:6−CF3−3−CHF2−4−Py]、[4494:2−CN−3−CHF2−4−Py]、[4495:5−CN−3−CHF2−4−Py]、[4496:6−CN−3−CHF2−4−Py]、[4497:2−OMe−3−CHF2−4−Py]、[4498:5−OMe−3−CHF2−4−Py]、[4499:6−OMe−3−CHF2−4−Py]、[4500:4−CHF2−4−Py]、 [4401: 3-OMe-5-CF3-4-Py], [4402: 2-OMe-5-CF3-4-Py], [4403: 6-OMe-5-CF3-4-Py], [4404 : 6-CF3-4-Py], [4405: 3-Cl-6-CF3-4-Py], [4406: 2-Cl-6-CF3-4-Py], [4407: 5-Cl-6 -CF3-4-Py], [4408: 3-Me-6-CF3-4-Py], [4409: 2-Me-6-CF3-4-Py], [4410: 5-Me-6-CF3 -4-Py], [4411: 3-CF3-6-CF3-4-Py], [4412: 2-CF3-6-CF3-4-Py], [4413: 5-CF3-6-CF3-4. -Py], [4414: 3-CN-6-CF3-4-Py], [4415: 2-CN 6-CF3-4-Py], [4416: 5-CN-6-CF3-4-Py], [4417: 3-OMe-6-CF3-4-Py], [4418: 2-OMe-6 CF3-4-Py], [4419: 5-OMe-6-CF3-4-Py], [4420: 3-OCF3-4-Py], [4421: 2-Cl-3-OCF3-4-Py] [4422: 5-Cl-3-OCF3-4-Py], [4423: 6-Cl-3-OCF3-4-Py], [4424: 2-Me-3-OCF3-4-Py], [ 4425: 5-Me-3-OCF3-4-Py], [4426: 6-Me-3-OCF3-4-Py], [4427: 2-CF3-3-OCF3-4-Py], [4428: 5-CF3-3-OCF3-4-Py], [4429: 6-CF3- -OCF3-4-Py], [4430: 2-CN-3-OCF3-4-Py], [4431: 5-CN-3-OCF3-4-Py], [4432: 6-CN-3-OCF3 -4-Py], [4433: 2-OMe-3-OCF3-4-Py], [4434: 5-OMe-3-OCF3-4-Py], [4435: 6-OMe-3-OCF3-4. -Py], [4436: 2-OCF3-4-Py], [4437: 3-Cl-2-OCF3-4-Py], [4438: 5-Cl-2-OCF3-4-Py], [4439] : 6-Cl-2-OCF3-4-Py], [4440: 3-Me-2-OCF3-4-Py], [4441: 5-Me-2-OCF3-4-Py], [4442: 6 -Me-2-OCF3-4-Py], [4443: 3-CF3 -2-OCF3-4-Py], [4444: 5-CF3-2-OCF3-4-Py], [4445: 6-CF3-2-OCF3-4-Py], [4446: 3-CN-2 -OCF3-4-Py], [4447: 5-CN-2-OCF3-4-Py], [4448: 6-CN-2-OCF3-4-Py], [4449: 3-OMe-2-OCF3 -4-Py], [4450: 5-OMe-2-OCF3-4-Py], [4451: 6-OMe-2-OCF3-4-Py], [4452: 5-OCF3-4-Py], [4453: 3-Cl-5-OCF3-4-Py], [4454: 2-Cl-5-OCF3-4-Py], [4455: 6-Cl-5-OCF3-4-Py], [4456 : 3-Me-5-OCF3-4-Py], [4457: 2 Me-5-OCF3-4-Py], [4458: 6-Me-5-OCF3-4-Py], [459: 3-CF3-5-OCF3-4-Py], [4460: 2-CF3- 5-OCF3-4-Py], [4461: 6-CF3-5-OCF3-4-Py], [4462: 3-CN-5-OCF3-4-Py], [4463: 2-CN-5 OCF3-4-Py], [4464: 6-CN-5-OCF3-4-Py], [4465: 3-OMe-5-OCF3-4-Py], [4466: 2-OMe-5-OCF3- 4-Py], [4467: 6-OMe-5-OCF3-4-Py], [4468: 6-OCF3-4-Py], [4469: 3-Cl-6-OCF3-4-Py], [ 4470: 2-Cl-6-OCF3-4-Py], [44 1: 5-Cl-6-OCF3-4-Py], [4472: 3-Me-6-OCF3-4-Py], [4473: 2-Me-6-OCF3-4-Py], [4474: 5-Me-6-OCF3-4-Py], [4475: 3-CF3-6-OCF3-4-Py], [4476: 2-CF3-6-OCF3-4-Py], [4477: 5- CF3-6-OCF3-4-Py], [4478: 3-CN-6-OCF3-4-Py], [4479: 2-CN-6-OCF3-4-Py], [4480: 5-CN- 6-OCF3-4-Py], [4481: 3-OMe-6-OCF3-4-Py], [4482: 2-OMe-6-OCF3-4-Py], [4483: 5-OMe-6 OCF3-4-Py], [4484: 3-CHF2-4-Py], [4485: 2-Cl-3-CHF2-4-Py], [4486: 5-Cl-3-CHF2-4-Py], [4487: 6-Cl-3-CHF2-4-Py], [4488 : 2-Me-3-CHF2-4-Py], [4489: 5-Me-3-CHF2-4-Py], [4490: 6-Me-3-CHF2-4-Py], [4491: 2 -CF3-3-CHF2-4-Py], [4492: 5-CF3-3-CHF2-4-Py], [4493: 6-CF3-3-CHF2-4-Py], [4494: 2-CN -3-CHF2-4-Py], [4495: 5-CN-3-CHF2-4-Py], [496: 6-CN-3-CHF2-4-Py], [4497: 2-OMe-3 -CHF2-4-Py], [4498: 5-OMe-3-CHF -4-Py], [4499: 6-OMe-3-CHF2-4-Py], [4500: 4-CHF2-4-Py],
[4501:3−Cl−4−CHF2−4−Py]、[4502:5−Cl−4−CHF2−4−Py]、[4503:6−Cl−4−CHF2−4−Py]、[4504:3−Me−4−CHF2−4−Py]、[4505:5−Me−4−CHF2−4−Py]、[4506:6−Me−4−CHF2−4−Py]、[4507:3−CF3−4−CHF2−4−Py]、[4508:5−CF3−4−CHF2−4−Py]、[4509:6−CF3−4−CHF2−4−Py]、[4510:3−CN−4−CHF2−4−Py]、[4511:5−CN−4−CHF2−4−Py]、[4512:6−CN−4−CHF2−4−Py]、[4513:3−OMe−4−CHF2−4−Py]、[4514:5−OMe−4−CHF2−4−Py]、[4515:6−OMe−4−CHF2−4−Py]、[4516:5−CHF2−4−Py]、[4517:3−Cl−5−CHF2−4−Py]、[4518:2−Cl−5−CHF2−4−Py]、[4519:6−Cl−5−CHF2−4−Py]、[4520:3−Me−5−CHF2−4−Py]、[4521:2−Me−5−CHF2−4−Py]、[4522:6−Me−5−CHF2−4−Py]、[4523:3−CF3−5−CHF2−4−Py]、[4524:2−CF3−5−CHF2−4−Py]、[4525:6−CF3−5−CHF2−4−Py]、[4526:3−CN−5−CHF2−4−Py]、[4527:2−CN−5−CHF2−4−Py]、[4528:6−CN−5−CHF2−4−Py]、[4529:3−OMe−5−CHF2−4−Py]、[4530:2−OMe−5−CHF2−4−Py]、[4531:6−OMe−5−CHF2−4−Py]、[4532:6−CHF2−4−Py]、[4533:3−Cl−6−CHF2−4−Py]、[4534:2−Cl−6−CHF2−4−Py]、[4535:5−Cl−6−CHF2−4−Py]、[4536:3−Me−6−CHF2−4−Py]、[4537:2−Me−6−CHF2−4−Py]、[4538:5−Me−6−CHF2−4−Py]、[4539:3−CF3−6−CHF2−4−Py]、[4540:2−CF3−6−CHF2−4−Py]、[4541:5−CF3−6−CHF2−4−Py]、[4542:3−CN−6−CHF2−4−Py]、[4543:2−CN−6−CHF2−4−Py]、[4544:5−CN−6−CHF2−4−Py]、[4545:3−OMe−6−CHF2−4−Py]、[4546:2−OMe−6−CHF2−4−Py]、[4547:5−OMe−6−CHF2−4−Py]、[4548:3−OCHF2−4−Py]、[4549:2−Cl−3−OCHF2−4−Py]、[4550:5−Cl−3−OCHF2−4−Py]、[4551:6−Cl−3−OCHF2−4−Py]、[4552:2−Me−3−OCHF2−4−Py]、[4553:5−Me−3−OCHF2−4−Py]、[4554:6−Me−3−OCHF2−4−Py]、[4555:2−CF3−3−OCHF2−4−Py]、[4556:5−CF3−3−OCHF2−4−Py]、[4557:6−CF3−3−OCHF2−4−Py]、[4558:2−CN−3−OCHF2−4−Py]、[4559:5−CN−3−OCHF2−4−Py]、[4560:6−CN−3−OCHF2−4−Py]、[4561:2−OMe−3−OCHF2−4−Py]、[4562:5−OMe−3−OCHF2−4−Py]、[4563:6−OMe−3−OCHF2−4−Py]、[4564:4−OCHF2−4−Py]、[4565:3−Cl−4−OCHF2−4−Py]、[4566:5−Cl−4−OCHF2−4−Py]、[4567:6−Cl−4−OCHF2−4−Py]、[4568:3−Me−4−OCHF2−4−Py]、[4569:5−Me−4−OCHF2−4−Py]、[4570:6−Me−4−OCHF2−4−Py]、[4571:3−CF3−4−OCHF2−4−Py]、[4572:5−CF3−4−OCHF2−4−Py]、[4573:6−CF3−4−OCHF2−4−Py]、[4574:3−CN−4−OCHF2−4−Py]、[4575:5−CN−4−OCHF2−4−Py]、[4576:6−CN−4−OCHF2−4−Py]、[4577:3−OMe−4−OCHF2−4−Py]、[4578:5−OMe−4−OCHF2−4−Py]、[4579:6−OMe−4−OCHF2−4−Py]、[4580:5−OCHF2−4−Py]、[4581:3−Cl−5−OCHF2−4−Py]、[4582:2−Cl−5−OCHF2−4−Py]、[4583:6−Cl−5−OCHF2−4−Py]、[4584:3−Me−5−OCHF2−4−Py]、[4585:2−Me−5−OCHF2−4−Py]、[4586:6−Me−5−OCHF2−4−Py]、[4587:3−CF3−5−OCHF2−4−Py]、[4588:2−CF3−5−OCHF2−4−Py]、[4589:6−CF3−5−OCHF2−4−Py]、[4590:3−CN−5−OCHF2−4−Py]、[4591:2−CN−5−OCHF2−4−Py]、[4592:6−CN−5−OCHF2−4−Py]、[4593:3−OMe−5−OCHF2−4−Py]、[4594:2−OMe−5−OCHF2−4−Py]、[4595:6−OMe−5−OCHF2−4−Py]、[4596:6−OCHF2−4−Py]、[4597:3−Cl−6−OCHF2−4−Py]、[4598:2−Cl−6−OCHF2−4−Py]、[4599:5−Cl−6−OCHF2−4−Py]、[4600:3−Me−6−OCHF2−4−Py]、 [4501: 3-Cl-4-CHF2-4-Py], [4502: 5-Cl-4-CHF2-4-Py], [4503: 6-Cl-4-CHF2-4-Py], [4504 : 3-Me-4-CHF2-4-Py], [4505: 5-Me-4-CHF2-4-Py], [4506: 6-Me-4-CHF2-4-Py], [4507: 3 -CF3-4-CHF2-4-Py], [4508: 5-CF3-4-CHF2-4-Py], [4509: 6-CF3-4-CHF2-4-Py], [4510: 3-CN -4-CHF2-4-Py], [4511: 5-CN-4-CHF2-4-Py], [4512: 6-CN-4-CHF2-4-Py], [4513: 3-OMe-4 -CHF2-4-Py], [4514: 5-OMe-4-CHF -4-Py], [4515: 6-OMe-4-CHF2-4-Py], [4516: 5-CHF2-4-Py], [4517: 3-Cl-5-CHF2-4-Py], [4518: 2-Cl-5-CHF2-4-Py], [4519: 6-Cl-5-CHF2-4-Py], [4520: 3-Me-5-CHF2-4-Py], [4521 : 2-Me-5-CHF2-4-Py], [4522: 6-Me-5-CHF2-4-Py], [4523: 3-CF3-5-CHF2-4-Py], [4524: 2 -CF3-5-CHF2-4-Py], [4525: 6-CF3-5-CHF2-4-Py], [4526: 3-CN-5-CHF2-4-Py], [4527: 2-CN -5-CHF2-4-Py], [4528: 6-CN-5-C F2-4-Py], [4529: 3-OMe-5-CHF2-4-Py], [4530: 2-OMe-5-CHF2-4-Py], [4531: 6-OMe-5-CHF2- 4-Py], [4532: 6-CHF2-4-Py], [4533: 3-Cl-6-CHF2-4-Py], [4534: 2-Cl-6-CHF2-4-Py], [ 4535: 5-Cl-6-CHF2-4-Py], [4536: 3-Me-6-CHF2-4-Py], [4537: 2-Me-6-CHF2-4-Py], [4538: 5-Me-6-CHF2-4-Py], [4539: 3-CF3-6-CHF2-4-Py], [4540: 2-CF3-6-CHF2-4-Py], [4541: 5- CF3-6-CHF2-4-Py], [4542: 3-CN- 6-CHF2-4-Py], [4543: 2-CN-6-CHF2-4-Py], [4544: 5-CN-6-CHF2-4-Py], [4545: 3-OMe-6 CHF2-4-Py], [4546: 2-OMe-6-CHF2-4-Py], [4547: 5-OMe-6-CHF2-4-Py], [4548: 3-OCHF2-4-Py] [4549: 2-Cl-3-OCHF2-4-Py], [4550: 5-Cl-3-OCHF2-4-Py], [4551: 6-Cl-3-OCHF2-4-Py], [ 4552: 2-Me-3-OCHF2-4-Py], [4553: 5-Me-3-OCHF2-4-Py], [4554: 6-Me-3-OCHF2-4-Py], [4555: 2-CF3-3-OCHF2-4-Py], [ 556: 5-CF3-3-OCHF2-4-Py], [4557: 6-CF3-3-OCHF2-4-Py], [4558: 2-CN-3-OCHF2-4-Py], [4559: 5-CN-3-OCHF2-4-Py], [4560: 6-CN-3-OCHF2-4-Py], [4561: 2-OMe-3-OCHF2-4-Py], [4562: 5- OMe-3-OCHF2-4-Py], [4563: 6-OMe-3-OCHF2-4-Py], [4564: 4-OCHF2-4-Py], [4565: 3-Cl-4-OCHF2- 4-Py], [4566: 5-Cl-4-OCHF2-4-Py], [4567: 6-Cl-4-OCHF2-4-Py], [4568: 3-Me-4-OCHF2-4- Py], [4569: 5-M -4-OCHF2-4-Py], [4570: 6-Me-4-OCHF2-4-Py], [4571: 3-CF3-4-OCHF2-4-Py], [4572: 5-CF3-4 -OCHF2-4-Py], [4573: 6-CF3-4-OCHF2-4-Py], [4574: 3-CN-4-OCHF2-4-Py], [4575: 5-CN-4-OCHF2 -4-Py], [4576: 6-CN-4-OCHF2-4-Py], [4577: 3-OMe-4-OCHF2-4-Py], [4578: 5-OMe-4-OCHF2-4 -Py], [4579: 6-OMe-4-OCHF2-4-Py], [4580: 5-OCHF2-4-Py], [4581: 3-Cl-5-OCHF2-4-Py], [4582 : 2-Cl-5-OCHF 2-4-Py], [4583: 6-Cl-5-OCHF2-4-Py], [4584: 3-Me-5-OCHF2-4-Py], [4585: 2-Me-5-OCHF2- 4-Py], [4586: 6-Me-5-OCHF2-4-Py], [4587: 3-CF3-5-OCHF2-4-Py], [4588: 2-CF3-5-OCHF2-4- Py], [4589: 6-CF3-5-OCHF2-4-Py], [4590: 3-CN-5-OCHF2-4-Py], [4591: 2-CN-5-OCHF2-4-Py] [4592: 6-CN-5-OCHF2-4-Py], [4593: 3-OMe-5-OCHF2-4-Py], [4594: 2-OMe-5-OCHF2-4-Py], [ 4595: 6-OMe-5-OCHF2- -Py], [4596: 6-OCHF2-4-Py], [4597: 3-Cl-6-OCHF2-4-Py], [4598: 2-Cl-6-OCHF2-4-Py], [4599] : 5-Cl-6-OCHF2-4-Py], [4600: 3-Me-6-OCHF2-4-Py],
[4601:2−Me−6−OCHF2−4−Py]、[4602:5−Me−6−OCHF2−4−Py]、[4603:3−CF3−6−OCHF2−4−Py]、[4604:2−CF3−6−OCHF2−4−Py]、[4605:5−CF3−6−OCHF2−4−Py]、[4606:3−CN−6−OCHF2−4−Py]、[4607:2−CN−6−OCHF2−4−Py]、[4608:5−CN−6−OCHF2−4−Py]、[4609:3−OMe−6−OCHF2−4−Py]、[4610:2−OMe−6−OCHF2−4−Py]、[4611:5−OMe−6−OCHF2−4−Py]、[4612:3−Et−4−Py]、[4613:2−Cl−3−Et−4−Py]、[4614:5−Cl−3−Et−4−Py]、[4615:6−Cl−3−Et−4−Py]、[4616:2−Me−3−Et−4−Py]、[4617:5−Me−3−Et−4−Py]、[4618:6−Me−3−Et−4−Py]、[4619:2−CF3−3−Et−4−Py]、[4620:5−CF3−3−Et−4−Py]、[4621:6−CF3−3−Et−4−Py]、[4622:2−CN−3−Et−4−Py]、[4623:5−CN−3−Et−4−Py]、[4624:6−CN−3−Et−4−Py]、[4625:2−OMe−3−Et−4−Py]、[4626:5−OMe−3−Et−4−Py]、[4627:6−OMe−3−Et−4−Py]、[4628:2−Et−4−Py]、[4629:3−Cl−2−Et−4−Py]、[4630:5−Cl−2−Et−4−Py]、[4631:6−Cl−2−Et−4−Py]、[4632:3−Me−2−Et−4−Py]、[4633:5−Me−2−Et−4−Py]、[4634:6−Me−2−Et−4−Py]、[4635:3−CF3−2−Et−4−Py]、[4636:5−CF3−2−Et−4−Py]、[4637:6−CF3−2−Et−4−Py]、[4638:3−CN−2−Et−4−Py]、[4639:5−CN−2−Et−4−Py]、[4640:6−CN−2−Et−4−Py]、[4641:3−OMe−2−Et−4−Py]、[4642:5−OMe−2−Et−4−Py]、[4643:6−OMe−2−Et−4−Py]、[4644:5−Et−4−Py]、[4645:3−Cl−5−Et−4−Py]、[4646:2−Cl−5−Et−4−Py]、[4647:6−Cl−5−Et−4−Py]、[4648:3−Me−5−Et−4−Py]、[4649:2−Me−5−Et−4−Py]、[4650:6−Me−5−Et−4−Py]、[4651:3−CF3−5−Et−4−Py]、[4652:2−CF3−5−Et−4−Py]、[4653:6−CF3−5−Et−4−Py]、[4654:3−CN−5−Et−4−Py]、[4655:2−CN−5−Et−4−Py]、[4656:6−CN−5−Et−4−Py]、[4657:3−OMe−5−Et−4−Py]、[4658:2−OMe−5−Et−4−Py]、[4659:6−OMe−5−Et−4−Py]、[4660:6−Et−4−Py]、[4661:3−Cl−6−Et−4−Py]、[4662:2−Cl−6−Et−4−Py]、[4663:5−Cl−6−Et−4−Py]、[4664:3−Me−6−Et−4−Py]、[4665:2−Me−6−Et−4−Py]、[4666:5−Me−6−Et−4−Py]、[4667:3−CF3−6−Et−4−Py]、[4668:2−CF3−6−Et−4−Py]、[4669:5−CF3−6−Et−4−Py]、[4670:3−CN−6−Et−4−Py]、[4671:2−CN−6−Et−4−Py]、[4672:5−CN−6−Et−4−Py]、[4673:3−OMe−6−Et−4−Py]、[4674:2−OMe−6−Et−4−Py]、[4675:5−OMe−6−Et−4−Py]、[4676:3−CH2CF3−4−Py]、[4677:2−Cl−3−CH2CF3−4−Py]、[4678:5−Cl−3−CH2CF3−4−Py]、[4679:6−Cl−3−CH2CF3−4−Py]、[4680:2−Me−3−CH2CF3−4−Py]、[4681:5−Me−3−CH2CF3−4−Py]、[4682:6−Me−3−CH2CF3−4−Py]、[4683:2−CF3−3−CH2CF3−4−Py]、[4684:5−CF3−3−CH2CF3−4−Py]、[4685:6−CF3−3−CH2CF3−4−Py]、[4686:2−CN−3−CH2CF3−4−Py]、[4687:5−CN−3−CH2CF3−4−Py]、[4688:6−CN−3−CH2CF3−4−Py]、[4689:2−OMe−3−CH2CF3−4−Py]、[4690:5−OMe−3−CH2CF3−4−Py]、[4691:6−OMe−3−CH2CF3−4−Py]、[4692:2−CH2CF3−4−Py]、[4693:3−Cl−2−CH2CF3−4−Py]、[4694:5−Cl−2−CH2CF3−4−Py]、[4695:6−Cl−2−CH2CF3−4−Py]、[4696:3−Me−2−CH2CF3−4−Py]、[4697:5−Me−2−CH2CF3−4−Py]、[4698:6−Me−2−CH2CF3−4−Py]、[4699:3−CF3−2−CH2CF3−4−Py]、[4700:5−CF3−2−CH2CF3−4−Py]、 [4601: 2-Me-6-OCHF2-4-Py], [4602: 5-Me-6-OCHF2-4-Py], [4603: 3-CF3-6-OCHF2-4-Py], [4604 : 2-CF3-6-OCHF2-4-Py], [4605: 5-CF3-6-OCHF2-4-Py], [4606: 3-CN-6-OCHF2-4-Py], [4607: 2] -CN-6-OCHF2-4-Py], [4608: 5-CN-6-OCHF2-4-Py], [4609: 3-OMe-6-OCHF2-4-Py], [4610: 2-OMe -6-OCHF2-4-Py], [4611: 5-OMe-6-OCHF2-4-Py], [4612: 3-Et-4-Py], [4613: 2-Cl-3-Et-4 -Py], [4614: 5-Cl-3- t-4-Py], [4615: 6-Cl-3-Et-4-Py], [4616: 2-Me-3-Et-4-Py], [4617: 5-Me-3-Et- 4-Py], [4618: 6-Me-3-Et-4-Py], [4619: 2-CF3-3-Et-4-Py], [4620: 5-CF3-3-Et-4- Py], [4621: 6-CF3-3-3-Et-4-Py], [4622: 2-CN-3-Et-4-Py], [4623: 5-CN-3-Et-4-Py] [4624: 6-CN-3-Et-4-Py], [4625: 2-OMe-3-Et-4-Py], [4626: 5-OMe-3-Et-4-Py], [ 4627: 6-OMe-3-Et-4-Py], [4628: 2-Et-4-Py], [4629: 3-Cl-2-Et 4-Py], [4630: 5-Cl-2-Et-4-Py], [4631: 6-Cl-2-Et-4-Py], [4632: 3-Me-2-Et-4- Py], [4633: 5-Me-2-Et-4-Py], [4634: 6-Me-2-Et-4-Py], [4635: 3-CF3-2-Et-4-Py] [4636: 5-CF3-2-Et-4-Py], [4637: 6-CF3-2-Et-4-Py], [4638: 3-CN-2-Et-4-Py], [ 4639: 5-CN-2-Et-4-Py], [4640: 6-CN-2-Et-4-Py], [4641: 3-OMe-2-Et-4-Py], [4642: 5-OMe-2-Et-4-Py], [4643: 6-OMe-2-Et-4-Py], [4644: 5-Et-4- Py], [4645: 3-Cl-5-Et-4-Py], [4646: 2-Cl-5-Et-4-Py], [4647: 6-Cl-5-Et-4-Py] [4648: 3-Me-5-Et-4-Py], [4649: 2-Me-5-Et-4-Py], [4650: 6-Me-5-Et-4-Py], [ 4651: 3-CF3-5-Et-4-Py], [4652: 2-CF3-5-Et-4-Py], [4653: 6-CF3-5-Et-4-Py], [4654: 3-CN-5-Et-4-Py], [4655: 2-CN-5-Et-4-Py], [4656: 6-CN-5-Et-4-Py], [4657: 3- OMe-5-Et-4-Py], [4658: 2-OMe-5-Et-4-Py], [4659: 6-OMe-5-Et 4-Py], [4660: 6-Et-4-Py], [4661: 3-Cl-6-Et-4-Py], [4662: 2-Cl-6-Et-4-Py], [ 4663: 5-Cl-6-Et-4-Py], [4664: 3-Me-6-Et-4-Py], [4665: 2-Me-6-Et-4-Py], [4666: 5-Me-6-Et-4-Py], [4667: 3-CF3-6-Et-4-Py], [4668: 2-CF3-6-Et-4-Py], [4669: 5- CF3-6-Et-4-Py], [4670: 3-CN-6-Et-4-Py], [4671: 2-CN-6-Et-4-Py], [4672: 5-CN- 6-Et-4-Py], [4673: 3-OMe-6-Et-4-Py], [4674: 2-OMe-6-Et-4- y], [4675: 5-OMe-6-Et-4-Py], [4676: 3-CH2CF3-4-Py], [4777: 2-Cl-3-CH2CF3-4-Py], [4678: 5-Cl-3-CH2CF3-4-Py], [4679: 6-Cl-3-CH2CF3-4-Py], [4680: 2-Me-3-CH2CF3-4-Py], [4681: 5- Me-3-CH2CF3-4-Py], [4682: 6-Me-3-CH2CF3-4-Py], [4683: 2-CF3-3-CH2CF3-4-Py], [4684: 5-CF3- 3-CH2CF3-4-Py], [4865: 6-CF3-3-CH2CF3-4-Py], [4686: 2-CN-3-CH2CF3-4-Py], [4687: 5-CN-3- CH2CF3-4-P y], [4688: 6-CN-3-CH2CF3-4-Py], [4629: 2-OMe-3-CH2CF3-4-Py], [4690: 5-OMe-3-CH2CF3-4-Py] [4691: 6-OMe-3-CH2CF3-4-Py], [4692: 2-CH2CF3-4-Py], [4693: 3-Cl-2-CH2CF3-4-Py], [4694: 5- Cl-2-CH2CF3-4-Py], [4695: 6-Cl-2-CH2CF3-4-Py], [4696: 3-Me-2-CH2CF3-4-Py], [4697: 5-Me- 2-CH2CF3-4-Py], [4698: 6-Me-2-CH2CF3-4-Py], [4699: 3-CF3-2-CH2CF3-4-Py], [4700: 5-CF3-2- CH2CF -4-Py],
[4701:6−CF3−2−CH2CF3−4−Py]、[4702:3−CN−2−CH2CF3−4−Py]、[4703:5−CN−2−CH2CF3−4−Py]、[4704:6−CN−2−CH2CF3−4−Py]、[4705:3−OMe−2−CH2CF3−4−Py]、[4706:5−OMe−2−CH2CF3−4−Py]、[4707:6−OMe−2−CH2CF3−4−Py]、[4708:5−CH2CF3−4−Py]、[4709:3−Cl−5−CH2CF3−4−Py]、[4710:2−Cl−5−CH2CF3−4−Py]、[4711:6−Cl−5−CH2CF3−4−Py]、[4712:3−Me−5−CH2CF3−4−Py]、[4713:2−Me−5−CH2CF3−4−Py]、[4714:6−Me−5−CH2CF3−4−Py]、[4715:3−CF3−5−CH2CF3−4−Py]、[4716:2−CF3−5−CH2CF3−4−Py]、[4717:6−CF3−5−CH2CF3−4−Py]、[4718:3−CN−5−CH2CF3−4−Py]、[4719:2−CN−5−CH2CF3−4−Py]、[4720:6−CN−5−CH2CF3−4−Py]、[4721:3−OMe−5−CH2CF3−4−Py]、[4722:2−OMe−5−CH2CF3−4−Py]、[4723:6−OMe−5−CH2CF3−4−Py]、[4724:6−CH2CF3−4−Py]、[4725:3−Cl−6−CH2CF3−4−Py]、[4726:2−Cl−6−CH2CF3−4−Py]、[4727:5−Cl−6−CH2CF3−4−Py]、[4728:3−Me−6−CH2CF3−4−Py]、[4729:2−Me−6−CH2CF3−4−Py]、[4730:5−Me−6−CH2CF3−4−Py]、[4731:3−CF3−6−CH2CF3−4−Py]、[4732:2−CF3−6−CH2CF3−4−Py]、[4733:5−CF3−6−CH2CF3−4−Py]、[4734:3−CN−6−CH2CF3−4−Py]、[4735:2−CN−6−CH2CF3−4−Py]、[4736:5−CN−6−CH2CF3−4−Py]、[4737:3−OMe−6−CH2CF3−4−Py]、[4738:2−OMe−6−CH2CF3−4−Py]、[4739:5−OMe−6−CH2CF3−4−Py]、[4740:3−OEt−4−Py]、[4741:2−Cl−3−OEt−4−Py]、[4742:5−Cl−3−OEt−4−Py]、[4743:6−Cl−3−OEt−4−Py]、[4744:2−Me−3−OEt−4−Py]、[4745:5−Me−3−OEt−4−Py]、[4746:6−Me−3−OEt−4−Py]、[4747:2−CF3−3−OEt−4−Py]、[4748:5−CF3−3−OEt−4−Py]、[4749:6−CF3−3−OEt−4−Py]、[4750:2−CN−3−OEt−4−Py]、[4751:5−CN−3−OEt−4−Py]、[4752:6−CN−3−OEt−4−Py]、[4753:2−OMe−3−OEt−4−Py]、[4754:5−OMe−3−OEt−4−Py]、[4755:6−OMe−3−OEt−4−Py]、[4756:2−OEt−4−Py]、[4757:3−Cl−2−OEt−4−Py]、[4758:5−Cl−2−OEt−4−Py]、[4759:6−Cl−2−OEt−4−Py]、[4760:3−Me−2−OEt−4−Py]、[4761:5−Me−2−OEt−4−Py]、[4762:6−Me−2−OEt−4−Py]、[4763:3−CF3−2−OEt−4−Py]、[4764:5−CF3−2−OEt−4−Py]、[4765:6−CF3−2−OEt−4−Py]、[4766:3−CN−2−OEt−4−Py]、[4767:5−CN−2−OEt−4−Py]、[4768:6−CN−2−OEt−4−Py]、[4769:3−OMe−2−OEt−4−Py]、[4770:5−OMe−2−OEt−4−Py]、[4771:6−OMe−2−OEt−4−Py]、[4772:5−OEt−4−Py]、[4773:3−Cl−5−OEt−4−Py]、[4774:2−Cl−5−OEt−4−Py]、[4775:6−Cl−5−OEt−4−Py]、[4776:3−Me−5−OEt−4−Py]、[4777:2−Me−5−OEt−4−Py]、[4778:6−Me−5−OEt−4−Py]、[4779:3−CF3−5−OEt−4−Py]、[4780:2−CF3−5−OEt−4−Py]、[4781:6−CF3−5−OEt−4−Py]、[4782:3−CN−5−OEt−4−Py]、[4783:2−CN−5−OEt−4−Py]、[4784:6−CN−5−OEt−4−Py]、[4785:3−OMe−5−OEt−4−Py]、[4786:2−OMe−5−OEt−4−Py]、[4787:6−OMe−5−OEt−4−Py]、[4788:6−OEt−4−Py]、[4789:3−Cl−6−OEt−4−Py]、[4790:2−Cl−6−OEt−4−Py]、[4791:5−Cl−6−OEt−4−Py]、[4792:3−Me−6−OEt−4−Py]、[4793:2−Me−6−OEt−4−Py]、[4794:5−Me−6−OEt−4−Py]、[4795:3−CF3−6−OEt−4−Py]、[4796:2−CF3−6−OEt−4−Py]、[4797:5−CF3−6−OEt−4−Py]、[4798:3−CN−6−OEt−4−Py]、[4799:2−CN−6−OEt−4−Py]、[4800:5−CN−6−OEt−4−Py]、 [4701: 6-CF3-2-CH2CF3-4-Py], [4702: 3-CN-2-CH2CF3-4-Py], [4703: 5-CN-2-CH2CF3-4-Py], [4704 : 6-CN-2-CH2CF3-4-Py], [4705: 3-OMe-2-CH2CF3-4-Py], [4706: 5-OMe-2-CH2CF3-4-Py], [4707: 6 -OMe-2-CH2CF3-4-Py], [4708: 5-CH2CF3-4-Py], [4709: 3-Cl-5-CH2CF3-4-Py], [4710: 2-Cl-5-CH2CF3 -4-Py], [4711: 6-Cl-5-CH2CF3-4-Py], [4712: 3-Me-5-CH2CF3-4-Py], [4713: 2-Me-5-CH2CF3-4. − y], [4714: 6-Me-5-CH2CF3-4-Py], [4715: 3-CF3-5-CH2CF3-4-Py], [4716: 2-CF3-5-CH2CF3-4-Py] [4717: 6-CF3-5-CH2CF3-4-Py], [4718: 3-CN-5-CH2CF3-4-Py], [4719: 2-CN-5-CH2CF3-4-Py], [ 4720: 6-CN-5-CH2CF3-4-Py], [4721: 3-OMe-5-CH2CF3-4-Py], [4722: 2-OMe-5-CH2CF3-4-Py], [4723: 6-OMe-5-CH2CF3-4-Py], [4724: 6-CH2CF3-4-Py], [4725: 3-Cl-6-CH2CF3-4-Py], [4726: 2-Cl-6 CH2 F3-4-Py], [4727: 5-Cl-6-CH2CF3-4-Py], [4728: 3-Me-6-CH2CF3-4-Py], [4729: 2-Me-6-CH2CF3- 4-Py], [4730: 5-Me-6-CH2CF3-4-Py], [4731: 3-CF3-6-CH2CF3-4-Py], [4732: 2-CF3-6-CH2CF3-4- Py], [4733: 5-CF3-6-CH2CF3-4-Py], [4734: 3-CN-6-CH2CF3-4-Py], [4735: 2-CN-6-CH2CF3-4-Py] [4736: 5-CN-6-CH2CF3-4-Py], [4737: 3-OMe-6-CH2CF3-4-Py], [4738: 2-OMe-6-CH2CF3-4-Py], [ 4739: 5 -OMe-6-CH2CF3-4-Py], [4740: 3-OEt-4-Py], [4741: 2-Cl-3-OEt-4-Py], [4742: 5-Cl-3-OEt -4-Py], [4743: 6-Cl-3-OEt-4-Py], [4744: 2-Me-3-OEt-4-Py], [4745: 5-Me-3-OEt-4. -Py], [4746: 6-Me-3-OEt-4-Py], [4747: 2-CF3-3-OEt-4-Py], [4748: 5-CF3-3-OEt-4-Py]. ], [4749: 6-CF3-3-OEt-4-Py], [4750: 2-CN-3-OEt-4-Py], [4751: 5-CN-3-OEt-4-Py], [4752: 6-CN-3-OEt-4-Py], [4753: 2-OMe-3-OE -4-Py], [4754: 5-OMe-3-OEt-4-Py], [4755: 6-OMe-3-OEt-4-Py], [4756: 2-OEt-4-Py], [4757: 3-Cl-2-OEt-4-Py], [4758: 5-Cl-2-OEt-4-Py], [4759: 6-Cl-2-OEt-4-Py], [4760 : 3-Me-2-OEt-4-Py], [4761: 5-Me-2-OEt-4-Py], [4762: 6-Me-2-OEt-4-Py], [4763: 3 -CF3-2-OEt-4-Py], [4764: 5-CF3-2-OEt-4-Py], [4765: 6-CF3-2-OEt-4-Py], [4766: 3-CN -2 -OEt-4-Py], [4767: 5-CN-2-OEt-4-Py], [47 8: 6-CN-2-OEt-4-Py], [4769: 3-OMe-2-OEt-4-Py], [4770: 5-OMe-2-OEt-4-Py], [4771: 6-OMe-2-OEt-4-Py], [4772: 5-OEt-4-Py], [4773: 3-Cl-5-OEt-4-Py], [4774: 2-Cl-5 OEt-4-Py], [4775: 6-Cl-5-OEt-4-Py], [4776: 3-Me-5-OEt-4-Py], [4777: 2-Me-5-OEt- 4-Py], [4778: 6-Me-5-OEt-4-Py], [4779: 3-CF3-5-OEt-4-Py], [4780: 2-CF3-5-OEt-4- Py], [4781: 6-CF3-5-OEt-4-Py], [4782: 3-CN-5-O. Et-4-Py], [4783: 2-CN-5-OEt-4-Py], [4784: 6-CN-5-OEt-4-Py], [4785: 3-OMe-5-OEt- 4-Py], [4786: 2-OMe-5-OEt-4-Py], [4787: 6-OMe-5-OEt-4-Py], [4788: 6-OEt-4-Py], [ 4789: 3-Cl-6-OEt-4-Py], [4790: 2-Cl-6-OEt-4-Py], [4791: 5-Cl-6-OEt-4-Py], [4792: 3-Me-6-OEt-4-Py], [4793: 2-Me-6-OEt-4-Py], [4794: 5-Me-6-OEt-4-Py], [4795: 3- CF3-6-OEt-4-Py], [4796: 2-CF3-6-OEt-4-Py], [4 97: 5-CF3-6-OEt-4-Py], [4798: 3-CN-6-OEt-4-Py], [4799: 2-CN-6-OEt-4-Py], [4800: 5-CN-6-OEt-4-Py],
[4801:3−OMe−6−OEt−4−Py]、[4802:2−OMe−6−OEt−4−Py]、[4803:5−OMe−6−OEt−4−Py]、[4804:3−OCH2CF3−4−Py]、[4805:2−Cl−3−OCH2CF3−4−Py]、[4806:5−Cl−3−OCH2CF3−4−Py]、[4807:6−Cl−3−OCH2CF3−4−Py]、[4808:2−Me−3−OCH2CF3−4−Py]、[4809:5−Me−3−OCH2CF3−4−Py]、[4810:6−Me−3−OCH2CF3−4−Py]、[4811:2−CF3−3−OCH2CF3−4−Py]、[4812:5−CF3−3−OCH2CF3−4−Py]、[4813:6−CF3−3−OCH2CF3−4−Py]、[4814:2−CN−3−OCH2CF3−4−Py]、[4815:5−CN−3−OCH2CF3−4−Py]、[4816:6−CN−3−OCH2CF3−4−Py]、[4817:2−OMe−3−OCH2CF3−4−Py]、[4818:5−OMe−3−OCH2CF3−4−Py]、[4819:6−OMe−3−OCH2CF3−4−Py]、[4820:2−OCH2CF3−4−Py]、[4821:3−Cl−2−OCH2CF3−4−Py]、[4822:5−Cl−2−OCH2CF3−4−Py]、[4823:6−Cl−2−OCH2CF3−4−Py]、[4824:3−Me−2−OCH2CF3−4−Py]、[4825:5−Me−2−OCH2CF3−4−Py]、[4826:6−Me−2−OCH2CF3−4−Py]、[4827:3−CF3−2−OCH2CF3−4−Py]、[4828:5−CF3−2−OCH2CF3−4−Py]、[4829:6−CF3−2−OCH2CF3−4−Py]、[4830:3−CN−2−OCH2CF3−4−Py]、[4831:5−CN−2−OCH2CF3−4−Py]、[4832:6−CN−2−OCH2CF3−4−Py]、[4833:3−OMe−2−OCH2CF3−4−Py]、[4834:5−OMe−2−OCH2CF3−4−Py]、[4835:6−OMe−2−OCH2CF3−4−Py]、[4836:5−OCH2CF3−4−Py]、[4837:3−Cl−5−OCH2CF3−4−Py]、[4838:2−Cl−5−OCH2CF3−4−Py]、[4839:6−Cl−5−OCH2CF3−4−Py]、[4840:3−Me−5−OCH2CF3−4−Py]、[4841:2−Me−5−OCH2CF3−4−Py]、[4842:6−Me−5−OCH2CF3−4−Py]、[4843:3−CF3−5−OCH2CF3−4−Py]、[4844:2−CF3−5−OCH2CF3−4−Py]、[4845:6−CF3−5−OCH2CF3−4−Py]、[4846:3−CN−5−OCH2CF3−4−Py]、[4847:2−CN−5−OCH2CF3−4−Py]、[4848:6−CN−5−OCH2CF3−4−Py]、[4849:3−OMe−5−OCH2CF3−4−Py]、[4850:2−OMe−5−OCH2CF3−4−Py]、[4851:6−OMe−5−OCH2CF3−4−Py]、[4852:6−OCH2CF3−4−Py]、[4853:3−Cl−6−OCH2CF3−4−Py]、[4854:2−Cl−6−OCH2CF3−4−Py]、[4855:5−Cl−6−OCH2CF3−4−Py]、[4856:3−Me−6−OCH2CF3−4−Py]、[4857:2−Me−6−OCH2CF3−4−Py]、[4858:5−Me−6−OCH2CF3−4−Py]、[4859:3−CF3−6−OCH2CF3−4−Py]、[4860:2−CF3−6−OCH2CF3−4−Py]、[4861:5−CF3−6−OCH2CF3−4−Py]、[4862:3−CN−6−OCH2CF3−4−Py]、[4863:2−CN−6−OCH2CF3−4−Py]、[4864:5−CN−6−OCH2CF3−4−Py]、[4865:3−OMe−6−OCH2CF3−4−Py]、[4866:2−OMe−6−OCH2CF3−4−Py]、[4867:5−OMe−6−OCH2CF3−4−Py]、[4868:3−Pr−4−Py]、[4869:2−Cl−3−Pr−4−Py]、[4870:5−Cl−3−Pr−4−Py]、[4871:6−Cl−3−Pr−4−Py]、[4872:2−Me−3−Pr−4−Py]、[4873:5−Me−3−Pr−4−Py]、[4874:6−Me−3−Pr−4−Py]、[4875:2−CF3−3−Pr−4−Py]、[4876:5−CF3−3−Pr−4−Py]、[4877:6−CF3−3−Pr−4−Py]、[4878:2−CN−3−Pr−4−Py]、[4879:5−CN−3−Pr−4−Py]、[4880:6−CN−3−Pr−4−Py]、[4881:2−OMe−3−Pr−4−Py]、[4882:5−OMe−3−Pr−4−Py]、[4883:6−OMe−3−Pr−4−Py]、[4884:2−Pr−4−Py]、[4885:3−Cl−2−Pr−4−Py]、[4886:5−Cl−2−Pr−4−Py]、[4887:6−Cl−2−Pr−4−Py]、[4888:3−Me−2−Pr−4−Py]、[4889:5−Me−2−Pr−4−Py]、[4890:6−Me−2−Pr−4−Py]、[4891:3−CF3−2−Pr−4−Py]、[4892:5−CF3−2−Pr−4−Py]、[4893:6−CF3−2−Pr−4−Py]、[4894:3−CN−2−Pr−4−Py]、[4895:5−CN−2−Pr−4−Py]、[4896:6−CN−2−Pr−4−Py]、[4897:3−OMe−2−Pr−4−Py]、[4898:5−OMe−2−Pr−4−Py]、[4899:6−OMe−2−Pr−4−Py]、[4900:5−Pr−4−Py]、 [4801: 3-OMe-6-OEt-4-Py], [4802: 2-OMe-6-OEt-4-Py], [4803: 5-OMe-6-OEt-4-Py], [4804 : 3-OCH2CF3-4-Py], [4805: 2-Cl-3-OCH2CF3-4-Py], [4806: 5-Cl-3-OCH2CF3-4-Py], [4807: 6-Cl-3] -OCH2CF3-4-Py], [4808: 2-Me-3-OCH2CF3-4-Py], [4809: 5-Me-3-OCH2CF3-4-Py], [4810: 6-Me-3-OCH2CF3 -4-Py], [4811: 2-CF3-3-OCH2CF3-4-Py], [4812: 5-CF3-3-OCH2CF3-4-Py], [4813: 6-CF3-3-OCH2CF3 4-Py], [4814: 2-CN-3-OCH2CF3-4-Py], [4815: 5-CN-3-OCH2CF3-4-Py], [4816: 6-CN-3-OCH2CF3-4- Py], [4817: 2-OMe-3-OCH2CF3-4-Py], [4818: 5-OMe-3-OCH2CF3-4-Py], [4819: 6-OMe-3-OCH2CF3-4-Py] [4820: 2-OCH2CF3-4-Py], [4821: 3-Cl-2-OCH2CF3-4-Py], [4822: 5-Cl-2-OCH2CF3-4-Py], [4823: 6- Cl-2-OCH2CF3-4-Py], [4824: 3-Me-2-OCH2CF3-4-Py], [4825: 5-Me-2-OCH2CF3-4-Py], [482 : 6-Me-2-OCH2CF3-4-Py], [4827: 3-CF3-2-OCH2CF3-4-Py], [4828: 5-CF3-2-OCH2CF3-4-Py], [4829: 6 -CF3-2-OCH2CF3-4-Py], [4830: 3-CN-2-OCH2CF3-4-Py], [4831: 5-CN-2-OCH2CF3-4-Py], [4832: 6-CN -2-OCH2CF3-4-Py], [4833: 3-OMe-2-OCH2CF3-4-Py], [4834: 5-OMe-2-OCH2CF3-4-Py], [4835: 6-OMe-2 -OCH2CF3-4-Py], [4836: 5-OCH2CF3-4-Py], [4837: 3-Cl-5-OCH2CF3-4-Py], [4838: 2-Cl-5 OCH2CF3-4-Py], [4839: 6-Cl-5-OCH2CF3-4-Py], [4840: 3-Me-5-OCH2CF3-4-Py], [4841: 2-Me-5-OCH2CF3- 4-Py], [4842: 6-Me-5-OCH2CF3-4-Py], [4843: 3-CF3-5-OCH2CF3-4-Py], [4844: 2-CF3-5-OCH2CF3-4- Py], [4845: 6-CF3-5-OCH2CF3-4-Py], [4846: 3-CN-5-OCH2CF3-4-Py], [4847: 2-CN-5-OCH2CF3-4-Py] [4848: 6-CN-5-OCH2CF3-4-Py], [4849: 3-OMe-5-OCH2CF3-4-Py], [4850: 2-OMe-5-OCH2 F3-4-Py], [4851: 6-OMe-5-OCH2CF3-4-Py], [4852: 6-OCH2CF3-4-Py], [4853: 3-Cl-6-OCH2CF3-4-Py] [4854: 2-Cl-6-OCH2CF3-4-Py], [4855: 5-Cl-6-OCH2CF3-4-Py], [4856: 3-Me-6-OCH2CF3-4-Py], [ 4857: 2-Me-6-OCH2CF3-4-Py], [4858: 5-Me-6-OCH2CF3-4-Py], [4859: 3-CF3-6-OCH2CF3-4-Py], [4860: 2-CF3-6-OCH2CF3-4-Py], [4861: 5-CF3-6-OCH2CF3-4-Py], [4862: 3-CN-6-OCH2CF3-4-Py], 4863: 2-CN-6-OCH2CF3-4-Py], [4864: 5-CN-6-OCH2CF3-4-Py], [4865: 3-OMe-6-OCH2CF3-4-Py], [4866: 2-OMe-6-OCH2CF3-4-Py], [4867: 5-OMe-6-OCH2CF3-4-Py], [4868: 3-Pr-4-Py], [4869: 2-Cl-3- Pr-4-Py], [4870: 5-Cl-3-Pr-4-Py], [4871: 6-Cl-3-Pr-4-Py], [4872: 2-Me-3-Pr- 4-Py], [4873: 5-Me-3-Pr-4-Py], [4874: 6-Me-3-Pr-4-Py], [4875: 2-CF3-3-Pr-4- Py], [4876: 5-CF3-3-3-Pr-4-Py], [ 4877: 6-CF3-3-Pr-4-Py], [4878: 2-CN-3-Pr-4-Py], [4879: 5-CN-3-Pr-4-Py], [4880: 6-CN-3-Pr-4-Py], [4881: 2-OMe-3-Pr-4-Py], [4882: 5-OMe-3-Pr-4-Py], [4883: 6- OMe-3-Pr-4-Py], [4884: 2-Pr-4-Py], [4885: 3-Cl-2-Pr-4-Py], [4886: 5-Cl-2-Pr- 4-Py], [4887: 6-Cl-2-Pr-4-Py], [4888: 3-Me-2-Pr-4-Py], [4889: 5-Me-2-Pr-4- Py], [4890: 6-Me-2-Pr-4-Py], [4891: 3-CF3-2-Pr-4-Py], [489 : 5-CF3-2-Pr-4-Py], [4893: 6-CF3-2-Pr-4-Py], [4894: 3-CN-2-Pr-4-Py], [4895: 5 -CN-2-Pr-4-Py], [4896: 6-CN-2-Pr-4-Py], [4897: 3-OMe-2-Pr-4-Py], [4898: 5-OMe -2-Pr-4-Py], [4899: 6-OMe-2-Pr-4-Py], [4900: 5-Pr-4-Py],
[4901:3−Cl−5−Pr−4−Py]、[4902:2−Cl−5−Pr−4−Py]、[4903:6−Cl−5−Pr−4−Py]、[4904:3−Me−5−Pr−4−Py]、[4905:2−Me−5−Pr−4−Py]、[4906:6−Me−5−Pr−4−Py]、[4907:3−CF3−5−Pr−4−Py]、[4908:2−CF3−5−Pr−4−Py]、[4909:6−CF3−5−Pr−4−Py]、[4910:3−CN−5−Pr−4−Py]、[4911:2−CN−5−Pr−4−Py]、[4912:6−CN−5−Pr−4−Py]、[4913:3−OMe−5−Pr−4−Py]、[4914:2−OMe−5−Pr−4−Py]、[4915:6−OMe−5−Pr−4−Py]、[4916:6−Pr−4−Py]、[4917:3−Cl−6−Pr−4−Py]、[4918:2−Cl−6−Pr−4−Py]、[4919:5−Cl−6−Pr−4−Py]、[4920:3−Me−6−Pr−4−Py]、[4921:2−Me−6−Pr−4−Py]、[4922:5−Me−6−Pr−4−Py]、[4923:3−CF3−6−Pr−4−Py]、[4924:2−CF3−6−Pr−4−Py]、[4925:5−CF3−6−Pr−4−Py]、[4926:3−CN−6−Pr−4−Py]、[4927:2−CN−6−Pr−4−Py]、[4928:5−CN−6−Pr−4−Py]、[4929:3−OMe−6−Pr−4−Py]、[4930:2−OMe−6−Pr−4−Py]、[4931:5−OMe−6−Pr−4−Py]、[4932:3−OPr−4−Py]、[4933:2−Cl−3−OPr−4−Py]、[4934:5−Cl−3−OPr−4−Py]、[4935:6−Cl−3−OPr−4−Py]、[4936:2−Me−3−OPr−4−Py]、[4937:5−Me−3−OPr−4−Py]、[4938:6−Me−3−OPr−4−Py]、[4939:2−CF3−3−OPr−4−Py]、[4940:5−CF3−3−OPr−4−Py]、[4941:6−CF3−3−OPr−4−Py]、[4942:2−CN−3−OPr−4−Py]、[4943:5−CN−3−OPr−4−Py]、[4944:6−CN−3−OPr−4−Py]、[4945:2−OMe−3−OPr−4−Py]、[4946:5−OMe−3−OPr−4−Py]、[4947:6−OMe−3−OPr−4−Py]、[4948:2−OPr−4−Py]、[4949:3−Cl−2−OPr−4−Py]、[4950:5−Cl−2−OPr−4−Py]、[4951:6−Cl−2−OPr−4−Py]、[4952:3−Me−2−OPr−4−Py]、[4953:5−Me−2−OPr−4−Py]、[4954:6−Me−2−OPr−4−Py]、[4955:3−CF3−2−OPr−4−Py]、[4956:5−CF3−2−OPr−4−Py]、[4957:6−CF3−2−OPr−4−Py]、[4958:3−CN−2−OPr−4−Py]、[4959:5−CN−2−OPr−4−Py]、[4960:6−CN−2−OPr−4−Py]、[4961:3−OMe−2−OPr−4−Py]、[4962:5−OMe−2−OPr−4−Py]、[4963:6−OMe−2−OPr−4−Py]、[4964:5−OPr−4−Py]、[4965:3−Cl−5−OPr−4−Py]、[4966:2−Cl−5−OPr−4−Py]、[4967:6−Cl−5−OPr−4−Py]、[4968:3−Me−5−OPr−4−Py]、[4969:2−Me−5−OPr−4−Py]、[4970:6−Me−5−OPr−4−Py]、[4971:3−CF3−5−OPr−4−Py]、[4972:2−CF3−5−OPr−4−Py]、[4973:6−CF3−5−OPr−4−Py]、[4974:3−CN−5−OPr−4−Py]、[4975:2−CN−5−OPr−4−Py]、[4976:6−CN−5−OPr−4−Py]、[4977:3−OMe−5−OPr−4−Py]、[4978:2−OMe−5−OPr−4−Py]、[4979:6−OMe−5−OPr−4−Py]、[4980:6−OPr−4−Py]、[4981:3−Cl−6−OPr−4−Py]、[4982:2−Cl−6−OPr−4−Py]、[4983:5−Cl−6−OPr−4−Py]、[4984:3−Me−6−OPr−4−Py]、[4985:2−Me−6−OPr−4−Py]、[4986:5−Me−6−OPr−4−Py]、[4987:3−CF3−6−OPr−4−Py]、[4988:2−CF3−6−OPr−4−Py]、[4989:5−CF3−6−OPr−4−Py]、[4990:3−CN−6−OPr−4−Py]、[4991:2−CN−6−OPr−4−Py]、[4992:5−CN−6−OPr−4−Py]、[4993:3−OMe−6−OPr−4−Py]、[4994:2−OMe−6−OPr−4−Py]、[4995:5−OMe−6−OPr−4−Py]、[4996:3−SMe−4−Py]、[4997:2−Cl−3−SMe−4−Py]、[4998:5−Cl−3−SMe−4−Py]、[4999:6−Cl−3−SMe−4−Py]、[5000:2−Me−3−SMe−4−Py]、 [4901: 3-Cl-5-Pr-4-Py], [4902: 2-Cl-5-Pr-4-Py], [4903: 6-Cl-5-Pr-4-Py], [4904 : 3-Me-5-Pr-4-Py], [4905: 2-Me-5-Pr-4-Py], [4906: 6-Me-5-Pr-4-Py], [4907: 3 -CF3-5-Pr-4-Py], [4908: 2-CF3-5-Pr-4-Py], [4909: 6-CF3-5-Pr-4-Py], [4910: 3-CN -5-Pr-4-Py], [4911: 2-CN-5-Pr-4-Py], [4912: 6-CN-5-Pr-4-Py], [4913: 3-OMe-5. -Pr-4-Py], [4914: 2-OMe-5-Pr-4-Py], [4915: 6-OMe-5-Pr-4-P ], [4916: 6-Pr-4-Py], [4917: 3-Cl-6-Pr-4-Py], [4918: 2-Cl-6-Pr-4-Py], [4919: 5]. -Cl-6-Pr-4-Py], [4920: 3-Me-6-Pr-4-Py], [4921: 2-Me-6-Pr-4-Py], [4922: 5-Me. -6-Pr-4-Py], [4923: 3-CF3-6-Pr-4-Py], [4924: 2-CF3-6-Pr-4-Py], [4925: 5-CF3-6. -Pr-4-Py], [4926: 3-CN-6-Pr-4-Py], [4927: 2-CN-6-Pr-4-Py], [4928: 5-CN-6-Pr -4-Py], [4929: 3-OMe-6-Pr-4-Py], [4930: 2-OMe-6-Pr-4-Py], 4931: 5-OMe-6-Pr-4-Py], [4932: 3-OPr-4-Py], [4933: 2-Cl-3-OPr-4-Py], [4934: 5-Cl- 3-OPr-4-Py], [4935: 6-Cl-3-OPr-4-Py], [4936: 2-Me-3-OPr-4-Py], [4937: 5-Me-3- OPr-4-Py], [4938: 6-Me-3-OPr-4-Py], [4939: 2-CF3-3-OPr-4-Py], [4940: 5-CF3-3-OPr- 4-Py], [4941: 6-CF3-3-OPr-4-Py], [4942: 2-CN-3-OPr-4-Py], [4943: 5-CN-3-OPr-4- Py], [4944: 6-CN-3-OPr-4-Py], [4945: 2-OMe-3- OPr-4-Py], [4946: 5-OMe-3-OPr-4-Py], [4947: 6-OMe-3-OPr-4-Py], [4948: 2-OPr-4-Py] [4949: 3-Cl-2-OPr-4-Py], [4950: 5-Cl-2-OPr-4-Py], [4951: 6-Cl-2-OPr-4-Py], [ 4952: 3-Me-2-OPr-4-Py], [4953: 5-Me-2-OPr-4-Py], [4954: 6-Me-2-OPr-4-Py], [4955: 3-CF3-2-OPr-4-Py], [4956: 5-CF3-2-OPr-4-Py], [4957: 6-CF3-2-OPr-4-Py], [4958: 3- CN-2-OPr-4-Py], [4959: 5-CN-2-OPr-4-Py], [ 960: 6-CN-2-OPr-4-Py], [4961: 3-OMe-2-OPr-4-Py], [4962: 5-OMe-2-OPr-4-Py], [4963: 6-OMe-2-OPr-4-Py], [4964: 5-OPr-4-Py], [4965: 3-Cl-5-OPr-4-Py], [4966: 2-Cl-5 OPr-4-Py], [4967: 6-Cl-5-OPr-4-Py], [4968: 3-Me-5-OPr-4-Py], [4969: 2-Me-5-OPr- 4-Py], [4970: 6-Me-5-OPr-4-Py], [4971: 3-CF3-5-OPr-4-Py], [4972: 2-CF3-5-OPr-4- Py], [4973: 6-CF3-5-OPr-4-Py], [4974: 3-CN- -OPr-4-Py], [4975: 2-CN-5-OPr-4-Py], [4976: 6-CN-5-OPr-4-Py], [4977: 3-OMe-5-OPr -4-Py], [4978: 2-OMe-5-OPr-4-Py], [4799: 6-OMe-5-OPr-4-Py], [4980: 6-OPr-4-Py], [4981: 3-Cl-6-OPr-4-Py], [4982: 2-Cl-6-OPr-4-Py], [4983: 5-Cl-6-OPr-4-Py], [4984 : 3-Me-6-OPr-4-Py], [4985: 2-Me-6-OPr-4-Py], [4986: 5-Me-6-OPr-4-Py], [4987: 3 -CF3-6-OPr-4-Py], [4988: 2-CF3-6-OPr-4-Py], [4989: 5-CF3-6-OPr-4-Py], [4990: 3-CN-6-OPr-4-Py], [4991: 2-CN-6-OPr-4-Py], [4992 : 5-CN-6-OPr-4-Py], [4993: 3-OMe-6-OPr-4-Py], [4994: 2-OMe-6-OPr-4-Py], [4995: 5. -OMe-6-OPr-4-Py], [4996: 3-SMe-4-Py], [4997: 2-Cl-3-SMe-4-Py], [4998: 5-Cl-3-SMe -4-Py], [4999: 6-Cl-3-SMe-4-Py], [5000: 2-Me-3-SMe-4-Py],
[5001:5−Me−3−SMe−4−Py]、[5002:6−Me−3−SMe−4−Py]、[5003:2−CF3−3−SMe−4−Py]、[5004:5−CF3−3−SMe−4−Py]、[5005:6−CF3−3−SMe−4−Py]、[5006:2−CN−3−SMe−4−Py]、[5007:5−CN−3−SMe−4−Py]、[5008:6−CN−3−SMe−4−Py]、[5009:2−OMe−3−SMe−4−Py]、[5010:5−OMe−3−SMe−4−Py]、[5011:6−OMe−3−SMe−4−Py]、[5012:2−SMe−4−Py]、[5013:3−Cl−2−SMe−4−Py]、[5014:5−Cl−2−SMe−4−Py]、[5015:6−Cl−2−SMe−4−Py]、[5016:3−Me−2−SMe−4−Py]、[5017:5−Me−2−SMe−4−Py]、[5018:6−Me−2−SMe−4−Py]、[5019:3−CF3−2−SMe−4−Py]、[5020:5−CF3−2−SMe−4−Py]、[5021:6−CF3−2−SMe−4−Py]、[5022:3−CN−2−SMe−4−Py]、[5023:5−CN−2−SMe−4−Py]、[5024:6−CN−2−SMe−4−Py]、[5025:3−OMe−2−SMe−4−Py]、[5026:5−OMe−2−SMe−4−Py]、[5027:6−OMe−2−SMe−4−Py]、[5028:5−SMe−4−Py]、[5029:3−Cl−5−SMe−4−Py]、[5030:2−Cl−5−SMe−4−Py]、[5031:6−Cl−5−SMe−4−Py]、[5032:3−Me−5−SMe−4−Py]、[5033:2−Me−5−SMe−4−Py]、[5034:6−Me−5−SMe−4−Py]、[5035:3−CF3−5−SMe−4−Py]、[5036:2−CF3−5−SMe−4−Py]、[5037:6−CF3−5−SMe−4−Py]、[5038:3−CN−5−SMe−4−Py]、[5039:2−CN−5−SMe−4−Py]、[5040:6−CN−5−SMe−4−Py]、[5041:3−OMe−5−SMe−4−Py]、[5042:2−OMe−5−SMe−4−Py]、[5043:6−OMe−5−SMe−4−Py]、[5044:6−SMe−4−Py]、[5045:3−Cl−6−SMe−4−Py]、[5046:2−Cl−6−SMe−4−Py]、[5047:5−Cl−6−SMe−4−Py]、[5048:3−Me−6−SMe−4−Py]、[5049:2−Me−6−SMe−4−Py]、[5050:5−Me−6−SMe−4−Py]、[5051:3−CF3−6−SMe−4−Py]、[5052:2−CF3−6−SMe−4−Py]、[5053:5−CF3−6−SMe−4−Py]、[5054:3−CN−6−SMe−4−Py]、[5055:2−CN−6−SMe−4−Py]、[5056:5−CN−6−SMe−4−Py]、[5057:3−OMe−6−SMe−4−Py]、[5058:2−OMe−6−SMe−4−Py]、[5059:5−OMe−6−SMe−4−Py]、[5060:3−SCF3−4−Py]、[5061:2−Cl−3−SCF3−4−Py]、[5062:5−Cl−3−SCF3−4−Py]、[5063:6−Cl−3−SCF3−4−Py]、[5064:2−Me−3−SCF3−4−Py]、[5065:5−Me−3−SCF3−4−Py]、[5066:6−Me−3−SCF3−4−Py]、[5067:2−CF3−3−SCF3−4−Py]、[5068:5−CF3−3−SCF3−4−Py]、[5069:6−CF3−3−SCF3−4−Py]、[5070:2−CN−3−SCF3−4−Py]、[5071:5−CN−3−SCF3−4−Py]、[5072:6−CN−3−SCF3−4−Py]、[5073:2−OMe−3−SCF3−4−Py]、[5074:5−OMe−3−SCF3−4−Py]、[5075:6−OMe−3−SCF3−4−Py]、[5076:2−SCF3−4−Py]、[5077:3−Cl−2−SCF3−4−Py]、[5078:5−Cl−2−SCF3−4−Py]、[5079:6−Cl−2−SCF3−4−Py]、[5080:3−Me−2−SCF3−4−Py]、[5081:5−Me−2−SCF3−4−Py]、[5082:6−Me−2−SCF3−4−Py]、[5083:3−CF3−2−SCF3−4−Py]、[5084:5−CF3−2−SCF3−4−Py]、[5085:6−CF3−2−SCF3−4−Py]、[5086:3−CN−2−SCF3−4−Py]、[5087:5−CN−2−SCF3−4−Py]、[5088:6−CN−2−SCF3−4−Py]、[5089:3−OMe−2−SCF3−4−Py]、[5090:5−OMe−2−SCF3−4−Py]、[5091:6−OMe−2−SCF3−4−Py]、[5092:5−SCF3−4−Py]、[5093:3−Cl−5−SCF3−4−Py]、[5094:2−Cl−5−SCF3−4−Py]、[5095:6−Cl−5−SCF3−4−Py]、[5096:3−Me−5−SCF3−4−Py]、[5097:2−Me−5−SCF3−4−Py]、[5098:6−Me−5−SCF3−4−Py]、[5099:3−CF3−5−SCF3−4−Py]、[5100:2−CF3−5−SCF3−4−Py]、 [5001: 5-Me-3-SMe-4-Py], [5002: 6-Me-3-SMe-4-Py], [5003: 2-CF3-3-SMe-4-Py], [5004 : 5-CF3-3-SMe-4-Py], [5005: 6-CF3-3-SMe-4-Py], [5006: 2-CN-3-SMe-4-Py], [5007: 5 -CN-3-SMe-4-Py], [5008: 6-CN-3-SMe-4-Py], [5009: 2-OMe-3-SMe-4-Py], [5010: 5-OMe -3-SMe-4-Py], [5011: 6-OMe-3-SMe-4-Py], [5012: 2-SMe-4-Py], [5013: 3-Cl-2-SMe-4 -Py], [5014: 5-Cl-2-SMe-4-Py], [5015: 6-Cl 2-SMe-4-Py], [5016: 3-Me-2-SMe-4-Py], [5017: 5-Me-2-SMe-4-Py], [5018: 6-Me-2-] SMe-4-Py], [5019: 3-CF3-2-SMe-4-Py], [5020: 5-CF3-2-SMe-4-Py], [5021: 6-CF3-2-SMe- 4-Py], [5022: 3-CN-2-SMe-4-Py], [5023: 5-CN-2-SMe-4-Py], [5024: 6-CN-2-SMe-4- Py], [5025: 3-OMe-2-SMe-4-Py], [5026: 5-OMe-2-SMe-4-Py], [5027: 6-OMe-2-SMe-4-Py] [5028: 5-SMe-4-Py], [5029: 3-Cl-5-SMe-4-P ], [5030: 2-Cl-5-SMe-4-Py], [5031: 6-Cl-5-SMe-4-Py], [5032: 3-Me-5-SMe-4-Py], [5033: 2-Me-5-SMe-4-Py], [5034: 6-Me-5-SMe-4-Py], [5035: 3-CF3-5-SMe-4-Py], [5036 : 2-CF3-5-SMe-4-Py], [5037: 6-CF3-5-SMe-4-Py], [5038: 3-CN-5-SMe-4-Py], [5039: 2 -CN-5-SMe-4-Py], [5040: 6-CN-5-SMe-4-Py], [5041: 3-OMe-5-SMe-4-Py], [5042: 2-OMe -5-SMe-4-Py], [5043: 6-OMe-5-SMe-4-Py], [50 44: 6-SMe-4-Py], [5045: 3-Cl-6-SMe-4-Py], [5046: 2-Cl-6-SMe-4-Py], [5047: 5-Cl- 6-SMe-4-Py], [5048: 3-Me-6-SMe-4-Py], [5049: 2-Me-6-SMe-4-Py], [5050: 5-Me-6-6 SMe-4-Py], [5051: 3-CF3-6-SMe-4-Py], [5052: 2-CF3-6-SMe-4-Py], [5053: 5-CF3-6-SMe- 4-Py], [5054: 3-CN-6-SMe-4-Py], [5055: 2-CN-6-SMe-4-Py], [5056: 5-CN-6-SMe-4- Py], [5057: 3-OMe-6-SMe-4-Py], [5058: 2-OMe-6-S e-4-Py], [5059: 5-OMe-6-SMe-4-Py], [5060: 3-SCF3-4-Py], [5061: 2-Cl-3-SCF3-4-Py] [5062: 5-Cl-3-SCF3-4-Py], [5063: 6-Cl-3-SCF3-4-Py], [5064: 2-Me-3-SCF3-4-Py], [ 5065: 5-Me-3-SCF3-4-Py], [5066: 6-Me-3-SCF3-4-Py], [5067: 2-CF3-3-SCF3-4-Py], [5068: 5-CF3-3-SCF3-4-Py], [5069: 6-CF3-3-SCF3-4-Py], [5070: 2-CN-3-SCF3-4-Py], [5071: 5- CN-3-SCF3-4-Py], [5072: 6-CN-3-S F3-4-Py], [5073: 2-OMe-3-SCF3-4-Py], [5074: 5-OMe-3-SCF3-4-Py], [5075: 6-OMe-3-SCF3- 4-Py], [5076: 2-SCF3-4-Py], [5077: 3-Cl-2-SCF3-4-Py], [5078: 5-Cl-2-SCF3-4-Py], [ 5079: 6-Cl-2-SCF3-4-Py], [5080: 3-Me-2-SCF3-4-Py], [5081: 5-Me-2-SCF3-4-Py], [5082: 6-Me-2-SCF3-4-Py], [5083: 3-CF3-2-SCF3-4-Py], [5084: 5-CF3-2-SCF3-4-Py], [5085: 6- CF3-2-SCF3-4-Py], [5086: 3-CN- 2-SCF3-4-Py], [5087: 5-CN-2-SCF3-4-Py], [5088: 6-CN-2-SCF3-4-Py], [5089: 3-OMe-2- SCF3-4-Py], [5090: 5-OMe-2-SCF3-4-Py], [5091: 6-OMe-2-SCF3-4-Py], [5092: 5-SCF3-4-Py] [5093: 3-Cl-5-SCF3-4-Py], [5094: 2-Cl-5-SCF3-4-Py], [5095: 6-Cl-5-SCF3-4-Py], [ 5096: 3-Me-5-SCF3-4-Py], [5097: 2-Me-5-SCF3-4-Py], [5098: 6-Me-5-SCF3-4-Py], [5099: 3-CF3-5-SCF3-4-Py], [5100: 2-C 3-5-SCF3-4-Py],
[5101:6−CF3−5−SCF3−4−Py]、[5102:3−CN−5−SCF3−4−Py]、[5103:2−CN−5−SCF3−4−Py]、[5104:6−CN−5−SCF3−4−Py]、[5105:3−OMe−5−SCF3−4−Py]、[5106:2−OMe−5−SCF3−4−Py]、[5107:6−OMe−5−SCF3−4−Py]、[5108:6−SCF3−4−Py]、[5109:3−Cl−6−SCF3−4−Py]、[5110:2−Cl−6−SCF3−4−Py]、[5111:6−Cl−6−SCF3−4−Py]、[5112:3−Me−6−SCF3−4−Py]、[5113:2−Me−6−SCF3−4−Py]、[5114:6−Me−6−SCF3−4−Py]、[5115:3−CF3−6−SCF3−4−Py]、[5116:2−CF3−6−SCF3−4−Py]、[5117:6−CF3−6−SCF3−4−Py]、[5118:3−CN−6−SCF3−4−Py]、[5119:2−CN−6−SCF3−4−Py]、[5120:6−CN−6−SCF3−4−Py]、[5121:3−OMe−6−SCF3−4−Py]、[5122:2−OMe−6−SCF3−4−Py]、[5123:6−OMe−6−SCF3−4−Py]、[5124:3−S(O)Me−4−Py]、[5125:2−Cl−3−S(O)Me−4−Py]、[5126:5−Cl−3−S(O)Me−4−Py]、[5127:6−Cl−3−S(O)Me−4−Py]、[5128:2−Me−3−S(O)Me−4−Py]、[5129:5−Me−3−S(O)Me−4−Py]、[5130:6−Me−3−S(O)Me−4−Py]、[5131:2−CF3−3−S(O)Me−4−Py]、[5132:5−CF3−3−S(O)Me−4−Py]、[5133:6−CF3−3−S(O)Me−4−Py]、[5134:2−CN−3−S(O)Me−4−Py]、[5135:5−CN−3−S(O)Me−4−Py]、[5136:6−CN−3−S(O)Me−4−Py]、[5137:2−OMe−3−S(O)Me−4−Py]、[5138:5−OMe−3−S(O)Me−4−Py]、[5139:6−OMe−3−S(O)Me−4−Py]、[5140:2−S(O)Me−4−Py]、[5141:3−Cl−2−S(O)Me−4−Py]、[5142:5−Cl−2−S(O)Me−4−Py]、[5143:6−Cl−2−S(O)Me−4−Py]、[5144:3−Me−2−S(O)Me−4−Py]、[5145:5−Me−2−S(O)Me−4−Py]、[5146:6−Me−2−S(O)Me−4−Py]、[5147:3−CF3−2−S(O)Me−4−Py]、[5148:5−CF3−2−S(O)Me−4−Py]、[5149:6−CF3−2−S(O)Me−4−Py]、[5150:3−CN−2−S(O)Me−4−Py]、[5151:5−CN−2−S(O)Me−4−Py]、[5152:6−CN−2−S(O)Me−4−Py]、[5153:3−OMe−2−S(O)Me−4−Py]、[5154:5−OMe−2−S(O)Me−4−Py]、[5155:6−OMe−2−S(O)Me−4−Py]、[5156:5−S(O)Me−4−Py]、[5157:3−Cl−5−S(O)Me−4−Py]、[5158:2−Cl−5−S(O)Me−4−Py]、[5159:6−Cl−5−S(O)Me−4−Py]、[5160:3−Me−5−S(O)Me−4−Py]、[5161:2−Me−5−S(O)Me−4−Py]、[5162:6−Me−5−S(O)Me−4−Py]、[5163:3−CF3−5−S(O)Me−4−Py]、[5164:2−CF3−5−S(O)Me−4−Py]、[5165:6−CF3−5−S(O)Me−4−Py]、[5166:3−CN−5−S(O)Me−4−Py]、[5167:2−CN−5−S(O)Me−4−Py]、[5168:6−CN−5−S(O)Me−4−Py]、[5169:3−OMe−5−S(O)Me−4−Py]、[5170:2−OMe−5−S(O)Me−4−Py]、[5171:6−OMe−5−S(O)Me−4−Py]、[5172:6−S(O)Me−4−Py]、[5173:3−Cl−6−S(O)Me−4−Py]、[5174:2−Cl−6−S(O)Me−4−Py]、[5175:5−Cl−6−S(O)Me−4−Py]、[5176:3−Me−6−S(O)Me−4−Py]、[5177:2−Me−6−S(O)Me−4−Py]、[5178:5−Me−6−S(O)Me−4−Py]、[5179:3−CF3−6−S(O)Me−4−Py]、[5180:2−CF3−6−S(O)Me−4−Py]、[5181:5−CF3−6−S(O)Me−4−Py]、[5182:3−CN−6−S(O)Me−4−Py]、[5183:2−CN−6−S(O)Me−4−Py]、[5184:5−CN−6−S(O)Me−4−Py]、[5185:3−OMe−6−S(O)Me−4−Py]、[5186:2−OMe−6−S(O)Me−4−Py]、[5187:5−OMe−6−S(O)Me−4−Py]、[5188:3−S(O)CF3−4−Py]、[5189:2−Cl−3−S(O)CF3−4−Py]、[5190:5−Cl−3−S(O)CF3−4−Py]、[5191:6−Cl−3−S(O)CF3−4−Py]、[5192:2−Me−3−S(O)CF3−4−Py]、[5193:5−Me−3−S(O)CF3−4−Py]、[5194:6−Me−3−S(O)CF3−4−Py]、[5195:2−CF3−3−S(O)CF3−4−Py]、[5196:5−CF3−3−S(O)CF3−4−Py]、[5197:6−CF3−3−S(O)CF3−4−Py]、[5198:2−CN−3−S(O)CF3−4−Py]、[5199:5−CN−3−S(O)CF3−4−Py]、[5200:6−CN−3−S(O)CF3−4−Py]、 [5101: 6-CF3-5-SCF3-4-Py], [5102: 3-CN-5-SCF3-4-Py], [5103: 2-CN-5-SCF3-4-Py], [5104 : 6-CN-5-SCF3-4-Py], [5105: 3-OMe-5-SCF3-4-Py], [5106: 2-OMe-5-SCF3-4-Py], [5107: 6 -OMe-5-SCF3-4-Py], [5108: 6-SCF3-4-Py], [5109: 3-Cl-6-SCF3-4-Py], [5110: 2-Cl-6-SCF3 -4-Py], [5111: 6-Cl-6-SCF3-4-Py], [5112: 3-Me-6-SCF3-4-Py], [5113: 2-Me-6-SCF3-4 -Py], [5114: 6-Me-6-SCF3-4-Py [5115: 3-CF3-6-SCF3-4-Py], [5116: 2-CF3-6-SCF3-4-Py], [5117: 6-CF3-6-SCF3-4-Py], [ 5118: 3-CN-6-SCF3-4-Py], [5119: 2-CN-6-SCF3-4-Py], [5120: 6-CN-6-SCF3-4-Py], [5121: 3-OMe-6-SCF3-4-Py], [5122: 2-OMe-6-SCF3-4-Py], [5123: 6-OMe-6-SCF3-4-Py], [5124: 3- S (O) Me-4-Py], [5125: 2-Cl-3-S (O) Me-4-Py], [5126: 5-Cl-3-S (O) Me-4-Py] [5127: 6-Cl-3-S (O) Me-4-Py], [5128: 2-Me. 3-S (O) Me-4-Py], [5129: 5-Me-3-S (O) Me-4-Py], [5130: 6-Me-3-S (O) Me-4- Py], [5131: 2-CF3-3-S (O) Me-4-Py], [5132: 5-CF3-3-S (O) Me-4-Py], [5133: 6-CF3- 3-S (O) Me-4-Py], [5134: 2-CN-3-S (O) Me-4-Py], [5135: 5-CN-3-S (O) Me-4- Py], [5136: 6-CN-3-S (O) Me-4-Py], [5137: 2-OMe-3-S (O) Me-4-Py], [5138: 5-OMe- 3-S (O) Me-4-Py], [5139: 6-OMe-3-S (O) Me-4-Py], [5140: 2-S (O) Me-4-Py], [ 5141 : 3-Cl-2-S (O) Me-4-Py], [5142: 5-Cl-2-S (O) Me-4-Py], [5143: 6-Cl-2-S (O ) Me-4-Py], [5144: 3-Me-2-S (O) Me-4-Py], [5145: 5-Me-2-S (O) Me-4-Py], [5146 : 6-Me-2-S (O) Me-4-Py], [5147: 3-CF3-2-S (O) Me-4-Py], [5148: 5-CF3-2-S (O ) Me-4-Py], [5149: 6-CF3-2-S (O) Me-4-Py], [5150: 3-CN-2-S (O) Me-4-Py], [5151. : 5-CN-2-S (O) Me-4-Py], [5152: 6-CN-2-S (O) Me-4-Py], [5153: 3-OMe-2-S (O ) Me-4- y], [5154: 5-OMe-2-S (O) Me-4-Py], [5155: 6-OMe-2-S (O) Me-4-Py], [5156: 5-S ( O) Me-4-Py], [5157: 3-Cl-5-S (O) Me-4-Py], [5158: 2-Cl-5-S (O) Me-4-Py], [ 5159: 6-Cl-5-S (O) Me-4-Py], [5160: 3-Me-5-S (O) Me-4-Py], [5161: 2-Me-5-S ( O) Me-4-Py], [5162: 6-Me-5-S (O) Me-4-Py], [5163: 3-CF3-5-S (O) Me-4-Py], [ 5164: 2-CF3-5-S (O) Me-4-Py], [5165: 6-CF3-5-S (O) Me-4-Py], [5166: 3-CN-5-S ( O) e-4-Py], [5167: 2-CN-5-S (O) Me-4-Py], [5168: 6-CN-5-S (O) Me-4-Py], [5169: 3-OMe-5-S (O) Me-4-Py], [5170: 2-OMe-5-S (O) Me-4-Py], [5171: 6-OMe-5-S (O) Me-4-Py], [5172: 6-S (O) Me-4-Py], [5173: 3-Cl-6-S (O) Me-4-Py], [5174: 2-Cl- 6-S (O) Me-4-Py], [5175: 5-Cl-6-S (O) Me-4-Py], [5176: 3-Me-6-S (O) Me-4-. Py], [5177: 2-Me-6-S (O) Me-4-Py], [5178: 5-Me-6-S (O) Me-4-Py], [5179: 3-CF3- 6-S (O) Me-4-Py], [5180: 2-CF3-6-S (O) Me-4-Py], [5181: 5-CF3-6-S (O) Me-4-Py], [5182: 3-CN-6-S (O) Me-4-Py], [5183: 2-CN-6-S (O) Me-4-Py], [5184: 5-CN-6-S (O) Me-4-Py], [5185: 3-OMe-6-S (O) Me-4-Py], [5186: 2-OMe-6-S (O) Me-4-Py], [5187: 5-OMe-6-S (O) Me-4-Py], [5188: 3-S (O) CF3-4-Py], [5189: 2-Cl-3-S (O) CF3 -4-Py], [5190: 5-Cl-3-S (O) CF3-4-Py], [5191: 6-Cl-3-S (O) CF3-4-Py], [5192 2-Me-3-S (O) CF3-4-Py], [5193: 5-Me-3-S (O) CF3-4-Py], [5194: 6-Me-3-S (O) CF3-4-Py], [5195: 2-CF3-3-S (O) CF3-4-Py], [5196: 5-CF3-3-S (O) CF3-4-Py], [5197: 6-CF3-3-S (O) CF3-4-Py], [5198: 2-CN-3-S (O) CF3-4-Py], [5199: 5-CN-3-S (O) CF3-4-Py], [5200: 6-CN-3-S (O) CF3-4-Py],
[5201:2−OMe−3−S(O)CF3−4−Py]、[5202:5−OMe−3−S(O)CF3−4−Py]、[5203:6−OMe−3−S(O)CF3−4−Py]、[5204:2−S(O)CF3−4−Py]、[5205:3−Cl−2−S(O)CF3−4−Py]、[5206:5−Cl−2−S(O)CF3−4−Py]、[5207:6−Cl−2−S(O)CF3−4−Py]、[5208:3−Me−2−S(O)CF3−4−Py]、[5209:5−Me−2−S(O)CF3−4−Py]、[5210:6−Me−2−S(O)CF3−4−Py]、[5211:3−CF3−2−S(O)CF3−4−Py]、[5212:5−CF3−2−S(O)CF3−4−Py]、[5213:6−CF3−2−S(O)CF3−4−Py]、[5214:3−CN−2−S(O)CF3−4−Py]、[5215:5−CN−2−S(O)CF3−4−Py]、[5216:6−CN−2−S(O)CF3−4−Py]、[5217:3−OMe−2−S(O)CF3−4−Py]、[5218:5−OMe−2−S(O)CF3−4−Py]、[5219:6−OMe−2−S(O)CF3−4−Py]、[5220:5−S(O)CF3−4−Py]、[5221:3−Cl−5−S(O)CF3−4−Py]、[5222:2−Cl−5−S(O)CF3−4−Py]、[5223:6−Cl−5−S(O)CF3−4−Py]、[5224:3−Me−5−S(O)CF3−4−Py]、[5225:2−Me−5−S(O)CF3−4−Py]、[5226:6−Me−5−S(O)CF3−4−Py]、[5227:3−CF3−5−S(O)CF3−4−Py]、[5228:2−CF3−5−S(O)CF3−4−Py]、[5229:6−CF3−5−S(O)CF3−4−Py]、[5230:3−CN−5−S(O)CF3−4−Py]、[5231:2−CN−5−S(O)CF3−4−Py]、[5232:6−CN−5−S(O)CF3−4−Py]、[5233:3−OMe−5−S(O)CF3−4−Py]、[5234:2−OMe−5−S(O)CF3−4−Py]、[5235:6−OMe−5−S(O)CF3−4−Py]、[5236:6−S(O)CF3−4−Py]、[5237:3−Cl−6−S(O)CF3−4−Py]、[5238:2−Cl−6−S(O)CF3−4−Py]、[5239:5−Cl−6−S(O)CF3−4−Py]、[5240:3−Me−6−S(O)CF3−4−Py]、[5241:2−Me−6−S(O)CF3−4−Py]、[5242:5−Me−6−S(O)CF3−4−Py]、[5243:3−CF3−6−S(O)CF3−4−Py]、[5244:2−CF3−6−S(O)CF3−4−Py]、[5245:5−CF3−6−S(O)CF3−4−Py]、[5246:3−CN−6−S(O)CF3−4−Py]、[5247:2−CN−6−S(O)CF3−4−Py]、[5248:5−CN−6−S(O)CF3−4−Py]、[5249:3−OMe−6−S(O)CF3−4−Py]、[5250:2−OMe−6−S(O)CF3−4−Py]、[5251:5−OMe−6−S(O)CF3−4−Py]、[5252:3−S(O)2Me−4−Py]、[5253:2−Cl−3−S(O)2Me−4−Py]、[5254:5−Cl−3−S(O)2Me−4−Py]、[5255:6−Cl−3−S(O)2Me−4−Py]、[5256:2−Me−3−S(O)2Me−4−Py]、[5257:5−Me−3−S(O)2Me−4−Py]、[5258:6−Me−3−S(O)2Me−4−Py]、[5259:2−CF3−3−S(O)2Me−4−Py]、[5260:5−CF3−3−S(O)2Me−4−Py]、[5261:6−CF3−3−S(O)2Me−4−Py]、[5262:2−CN−3−S(O)2Me−4−Py]、[5263:5−CN−3−S(O)2Me−4−Py]、[5264:6−CN−3−S(O)2Me−4−Py]、[5265:2−OMe−3−S(O)2Me−4−Py]、[5266:5−OMe−3−S(O)2Me−4−Py]、[5267:6−OMe−3−S(O)2Me−4−Py]、[5268:2−S(O)2Me−4−Py]、[5269:3−Cl−2−S(O)2Me−4−Py]、[5270:5−Cl−2−S(O)2Me−4−Py]、[5271:6−Cl−2−S(O)2Me−4−Py]、[5272:3−Me−2−S(O)2Me−4−Py]、[5273:5−Me−2−S(O)2Me−4−Py]、[5274:6−Me−2−S(O)2Me−4−Py]、[5275:3−CF3−2−S(O)2Me−4−Py]、[5276:5−CF3−2−S(O)2Me−4−Py]、[5277:6−CF3−2−S(O)2Me−4−Py]、[5278:3−CN−2−S(O)2Me−4−Py]、[5279:5−CN−2−S(O)2Me−4−Py]、[5280:6−CN−2−S(O)2Me−4−Py]、[5281:3−OMe−2−S(O)2Me−4−Py]、[5282:5−OMe−2−S(O)2Me−4−Py]、[5283:6−OMe−2−S(O)2Me−4−Py]、[5284:5−S(O)2Me−4−Py]、[5285:3−Cl−5−S(O)2Me−4−Py]、[5286:2−Cl−5−S(O)2Me−4−Py]、[5287:6−Cl−5−S(O)2Me−4−Py]、[5288:3−Me−5−S(O)2Me−4−Py]、[5289:2−Me−5−S(O)2Me−4−Py]、[5290:6−Me−5−S(O)2Me−4−Py]、[5291:3−CF3−5−S(O)2Me−4−Py]、[5292:2−CF3−5−S(O)2Me−4−Py]、[5293:6−CF3−5−S(O)2Me−4−Py]、[5294:3−CN−5−S(O)2Me−4−Py]、[5295:2−CN−5−S(O)2Me−4−Py]、[5296:6−CN−5−S(O)2Me−4−Py]、[5297:3−OMe−5−S(O)2Me−4−Py]、[5298:2−OMe−5−S(O)2Me−4−Py]、[5299:6−OMe−5−S(O)2Me−4−Py]、[5300:6−S(O)2Me−4−Py]、 [5201: 2-OMe-3-S (O) CF3-4-Py], [5202: 5-OMe-3-S (O) CF3-4-Py], [5203: 6-OMe-3-S (O) CF3-4-Py], [5204: 2-S (O) CF3-4-Py], [5205: 3-Cl-2-S (O) CF3-4-Py], [5206: 5 -Cl-2-S (O) CF3-4-Py], [5207: 6-Cl-2-S (O) CF3-4-Py], [5208: 3-Me-2-S (O) CF3 -4-Py], [5209: 5-Me-2-S (O) CF3-4-Py], [5210: 6-Me-2-S (O) CF3-4-Py], [5211: 3 -CF3-2-S (O) CF3-4-Py], [5212: 5-CF3-2-S (O) CF3-4-Py], [5213: 6-C 3-2-S (O) CF3-4-Py], [5214: 3-CN-2-S (O) CF3-4-Py], [5215: 5-CN-2-S (O) CF3- 4-Py], [5216: 6-CN-2-S (O) CF3-4-Py], [5217: 3-OMe-2-S (O) CF3-4-Py], [5218: 5- OMe-2-S (O) CF3-4-Py], [5219: 6-OMe-2-S (O) CF3-4-Py], [5220: 5-S (O) CF3-4-Py] [5221: 3-Cl-5-S (O) CF3-4-Py], [5222: 2-Cl-5-S (O) CF3-4-Py], [5223: 6-Cl-5- S (O) CF3-4-Py], [5224: 3-Me-5-S (O) CF3-4-Py], [5225: 2-Me-5-S (O) CF -4-Py], [5226: 6-Me-5-S (O) CF3-4-Py], [5227: 3-CF3-5-S (O) CF3-4-Py], [5228: 2 -CF3-5-S (O) CF3-4-Py], [5229: 6-CF3-5-S (O) CF3-4-Py], [5230: 3-CN-5-S (O) CF3. -4-Py], [5231: 2-CN-5-S (O) CF3-4-Py], [5232: 6-CN-5-S (O) CF3-4-Py], [5233: 3. -OMe-5-S (O) CF3-4-Py], [5234: 2-OMe-5-S (O) CF3-4-Py], [5235: 6-OMe-5-S (O) CF3 -4-Py], [5236: 6-S (O) CF3-4-Py], [5237: 3-Cl-6-S (O) CF3-4-Py], [ 5238: 2-Cl-6-S (O) CF3-4-Py], [5239: 5-Cl-6-S (O) CF3-4-Py], [5240: 3-Me-6-S ( O) CF3-4-Py], [5241: 2-Me-6-S (O) CF3-4-Py], [5242: 5-Me-6-S (O) CF3-4-Py], [ 5243: 3-CF3-6-S (O) CF3-4-Py], [5244: 2-CF3-6-S (O) CF3-4-Py], [5245: 5-CF3-6-S ( O) CF3-4-Py], [5246: 3-CN-6-S (O) CF3-4-Py], [5247: 2-CN-6-S (O) CF3-4-Py], [ 5248: 5-CN-6-S (O) CF3-4-Py], [5249: 3-OMe-6-S (O) CF3-4-Py], [5250: -OMe-6-S (O) CF3-4-Py], [5251: 5-OMe-6-S (O) CF3-4-Py], [5252: 3-S (O) 2Me-4-Py ], [5253: 2-Cl-3-S (O) 2Me-4-Py], [5254: 5-Cl-3-S (O) 2Me-4-Py], [5255: 6-Cl-3]. -S (O) 2Me-4-Py], [5256: 2-Me-3-S (O) 2Me-4-Py], [5257: 5-Me-3-S (O) 2Me-4-Py]. ], [5258: 6-Me-3-S (O) 2Me-4-Py], [5259: 2-CF3-3-S (O) 2Me-4-Py], [5260: 5-CF3-3. -S (O) 2Me-4-Py], [5261: 6-CF3-3-3-S (O) 2Me-4-Py], [5262: 2-CN-3-S ( ) 2Me-4-Py], [5263: 5-CN-3-S (O) 2Me-4-Py], [5264: 6-CN-3-S (O) 2Me-4-Py], [5265] : 2-OMe-3-S (O) 2Me-4-Py], [5266: 5-OMe-3-S (O) 2Me-4-Py], [5267: 6-OMe-3-S (O ) 2Me-4-Py], [5268: 2-S (O) 2Me-4-Py], [5269: 3-Cl-2-S (O) 2Me-4-Py], [5270: 5-Cl -2 -S (O) 2Me-4-Py], [5271: 6-Cl-2-S (O) 2Me-4-Py], [5272: 3-Me-2-S (O) 2Me-4 -Py], [5273: 5-Me-2-S (O) 2Me-4-Py], [5274: 6-Me-2-S (O) 2Me-4-Py], [5275: 3-CF3-2-S (O) 2Me-4-Py], [5276: 5-CF3-2-S (O) 2Me-4-Py], [5277: 6-CF3-2-S (O) 2Me-4-Py], [5278: 3-CN-2-S (O) 2Me-4-Py], [5279: 5-CN-2-S (O) 2Me-4-Py], [5280: 6-CN-2-S (O) 2Me-4-Py], [5281: 3-OMe-2-S (O) 2Me-4-Py], [5282: 5-OMe-2-S (O) 2Me-4-Py], [5283: 6-OMe-2-S (O) 2Me-4-Py], [5284: 5-S (O) 2Me-4-Py], [5285: 3. -Cl-5-S (O) 2Me-4-Py], [5286: 2-Cl-5-S (O) 2Me-4-Py], [5287: 6- l-5-S (O) 2Me-4-Py], [5288: 3-Me-5-S (O) 2Me-4-Py], [5289: 2-Me-5-S (O) 2Me- 4-Py], [5290: 6-Me-5-S (O) 2Me-4-Py], [5291: 3-CF3-5-S (O) 2Me-4-Py], [5292: 2- CF3-5-S (O) 2Me-4-Py], [5293: 6-CF3-5-S (O) 2Me-4-Py], [5294: 3-CN-5-S (O) 2Me- 4-Py], [5295: 2-CN-5-S (O) 2Me-4-Py], [5296: 6-CN-5-S (O) 2Me-4-Py], [5297: 3- OMe-5-S (O) 2Me-4-Py], [5298: 2-OMe-5-S (O) 2Me-4-Py], [5299: 6-OMe- -S (O) 2Me-4-Py], [5300: 6-S (O) 2Me-4-Py],
[5301:3−Cl−6−S(O)2Me−4−Py]、[5302:2−Cl−6−S(O)2Me−4−Py]、[5303:5−Cl−6−S(O)2Me−4−Py]、[5304:3−Me−6−S(O)2Me−4−Py]、[5305:2−Me−6−S(O)2Me−4−Py]、[5306:5−Me−6−S(O)2Me−4−Py]、[5307:3−CF3−6−S(O)2Me−4−Py]、[5308:2−CF3−6−S(O)2Me−4−Py]、[5309:5−CF3−6−S(O)2Me−4−Py]、[5310:3−CN−6−S(O)2Me−4−Py]、[5311:2−CN−6−S(O)2Me−4−Py]、[5312:5−CN−6−S(O)2Me−4−Py]、[5313:3−OMe−6−S(O)2Me−4−Py]、[5314:2−OMe−6−S(O)2Me−4−Py]、[5315:5−OMe−6−S(O)2Me−4−Py]、[5316:3−S(O)2CF3−4−Py]、[5317:2−Cl−3−S(O)2CF3−4−Py]、[5318:5−Cl−3−S(O)2CF3−4−Py]、[5319:6−Cl−3−S(O)2CF3−4−Py]、[5320:2−Me−3−S(O)2CF3−4−Py]、[5321:5−Me−3−S(O)2CF3−4−Py]、[5322:6−Me−3−S(O)2CF3−4−Py]、[5323:2−CF3−3−S(O)2CF3−4−Py]、[5324:5−CF3−3−S(O)2CF3−4−Py]、[5325:6−CF3−3−S(O)2CF3−4−Py]、[5326:2−CN−3−S(O)2CF3−4−Py]、[5327:5−CN−3−S(O)2CF3−4−Py]、[5328:6−CN−3−S(O)2CF3−4−Py]、[5329:2−OMe−3−S(O)2CF3−4−Py]、[5330:5−OMe−3−S(O)2CF3−4−Py]、[5331:6−OMe−3−S(O)2CF3−4−Py]、[5332:2−S(O)2CF3−4−Py]、[5333:3−Cl−2−S(O)2CF3−4−Py]、[5334:5−Cl−2−S(O)2CF3−4−Py]、[5335:6−Cl−2−S(O)2CF3−4−Py]、[5336:3−Me−2−S(O)2CF3−4−Py]、[5337:5−Me−2−S(O)2CF3−4−Py]、[5338:6−Me−2−S(O)2CF3−4−Py]、[5339:3−CF3−2−S(O)2CF3−4−Py]、[5340:5−CF3−2−S(O)2CF3−4−Py]、[5341:6−CF3−2−S(O)2CF3−4−Py]、[5342:3−CN−2−S(O)2CF3−4−Py]、[5343:5−CN−2−S(O)2CF3−4−Py]、[5344:6−CN−2−S(O)2CF3−4−Py]、[5345:3−OMe−2−S(O)2CF3−4−Py]、[5346:5−OMe−2−S(O)2CF3−4−Py]、[5347:6−OMe−2−S(O)2CF3−4−Py]、[5348:5−S(O)2CF3−4−Py]、[5349:3−Cl−5−S(O)2CF3−4−Py]、[5350:2−Cl−5−S(O)2CF3−4−Py]、[5351:6−Cl−5−S(O)2CF3−4−Py]、[5352:3−Me−5−S(O)2CF3−4−Py]、[5353:2−Me−5−S(O)2CF3−4−Py]、[5354:6−Me−5−S(O)2CF3−4−Py]、[5355:3−CF3−5−S(O)2CF3−4−Py]、[5356:2−CF3−5−S(O)2CF3−4−Py]、[5357:6−CF3−5−S(O)2CF3−4−Py]、[5358:3−CN−5−S(O)2CF3−4−Py]、[5359:2−CN−5−S(O)2CF3−4−Py]、[5360:6−CN−5−S(O)2CF3−4−Py]、[5361:3−OMe−5−S(O)2CF3−4−Py]、[5362:2−OMe−5−S(O)2CF3−4−Py]、[5363:6−OMe−5−S(O)2CF3−4−Py]、[5364:6−S(O)2CF3−4−Py]、[5365:3−Cl−6−S(O)2CF3−4−Py]、[5366:2−Cl−6−S(O)2CF3−4−Py]、[5367:5−Cl−6−S(O)2CF3−4−Py]、[5368:3−Me−6−S(O)2CF3−4−Py]、[5369:2−Me−6−S(O)2CF3−4−Py]、[5370:5−Me−6−S(O)2CF3−4−Py]、[5371:3−CF3−6−S(O)2CF3−4−Py]、[5372:2−CF3−6−S(O)2CF3−4−Py]、[5373:5−CF3−6−S(O)2CF3−4−Py]、[5374:3−CN−6−S(O)2CF3−4−Py]、[5375:2−CN−6−S(O)2CF3−4−Py]、[5376:5−CN−6−S(O)2CF3−4−Py]、[5377:3−OMe−6−S(O)2CF3−4−Py]、[5378:2−OMe−6−S(O)2CF3−4−Py]、[5379:5−OMe−6−S(O)2CF3−4−Py]、[5380:3−CN−4−Py]、[5381:2−Cl−3−CN−4−Py]、[5382:5−Cl−3−CN−4−Py]、[5383:6−Cl−3−CN−4−Py]、[5384:2−Me−3−CN−4−Py]、[5385:5−Me−3−CN−4−Py]、[5386:6−Me−3−CN−4−Py]、[5387:2−CF3−3−CN−4−Py]、[5388:5−CF3−3−CN−4−Py]、[5389:6−CF3−3−CN−4−Py]、[5390:2−CN−3−CN−4−Py]、[5391:5−CN−3−CN−4−Py]、[5392:6−CN−3−CN−4−Py]、[5393:2−OMe−3−CN−4−Py]、[5394:5−OMe−3−CN−4−Py]、[5395:6−OMe−3−CN−4−Py]、[5396:2−CN−4−Py]、[5397:3−Cl−2−CN−4−Py]、[5398:5−Cl−2−CN−4−Py]、[5399:6−Cl−2−CN−4−Py]、[5400:3−Me−2−CN−4−Py]、 [5301: 3-Cl-6-S (O) 2Me-4-Py], [5302: 2-Cl-6-S (O) 2Me-4-Py], [5303: 5-Cl-6-S (O) 2Me-4-Py], [5304: 3-Me-6-S (O) 2Me-4-Py], [5305: 2-Me-6-S (O) 2Me-4-Py], [5306: 5-Me-6-S (O) 2Me-4-Py], [5307: 3-CF3-6-S (O) 2Me-4-Py], [5308: 2-CF3-6-S (O) 2Me-4-Py], [5309: 5-CF3-6-S (O) 2Me-4-Py], [5310: 3-CN-6-S (O) 2Me-4-Py], [5311: 2-CN-6-S (O) 2Me-4-Py], [5312: 5-CN-6-S (O) 2Me-4-Py], [5313: -OMe-6-S (O) 2Me-4-Py], [5314: 2-OMe-6-S (O) 2Me-4-Py], [5315: 5-OMe-6-S (O) 2Me -4-Py], [5316: 3-S (O) 2CF3-4-Py], [5317: 2-Cl-3-S (O) 2CF3-4-Py], [5318: 5-Cl-3 -S (O) 2CF3-4-Py], [5319: 6-Cl-3-S (O) 2CF3-4-Py], [5320: 2-Me-3-S (O) 2CF3-4-Py ], [5321: 5-Me-3-S (O) 2CF3-4-Py], [5322: 6-Me-3-S (O) 2CF3-4-Py], [5323: 2-CF3-3]. -S (O) 2CF3-4-Py], [5324: 5-CF3-3-S (O) 2CF3-4-Py], [5325: -CF3-3-S (O) 2CF3-4-Py], [5326: 2-CN-3-S (O) 2CF3-4-Py], [5327: 5-CN-3-S (O) 2CF3 -4-Py], [5328: 6-CN-3-S (O) 2CF3-4-Py], [5329: 2-OMe-3-S (O) 2CF3-4-Py], [5330: 5. -OMe-3-S (O) 2CF3-4-Py], [5331: 6-OMe-3-S (O) 2CF3-4-Py], [5332: 2-S (O) 2CF3-4-Py ], [5333: 3-Cl-2-S (O) 2CF3-4-Py], [5334: 5-Cl-2-S (O) 2CF3-4-Py], [5335: 6-Cl-2. -S (O) 2CF3-4-Py], [5336: 3-Me-2-S (O) 2CF3-4-Py], [5337. : 5-Me-2-S (O) 2CF3-4-Py], [5338: 6-Me-2-S (O) 2CF3-4-Py], [5339: 3-CF3-2-S (O ) 2CF3-4-Py], [5340: 5-CF3-2-S (O) 2CF3-4-Py], [5341: 6-CF3-2-S (O) 2CF3-4-Py], [5342 : 3-CN-2-S (O) 2CF3-4-Py], [5343: 5-CN-2-S (O) 2CF3-4-Py], [5344: 6-CN-2-S (O ) 2CF3-4-Py], [5345: 3-OMe-2-S (O) 2CF3-4-Py], [5346: 5-OMe-2-S (O) 2CF3-4-Py], [5347 : 6-OMe-2-S (O) 2CF3-4-Py], [5348: 5-S (O) 2CF3-4-Py], [ 349: 3-Cl-5-S (O) 2CF3-4-Py], [5350: 2-Cl-5-S (O) 2CF3-4-Py], [5351: 6-Cl-5-S ( O) 2CF3-4-Py], [5352: 3-Me-5-S (O) 2CF3-4-Py], [5353: 2-Me-5-S (O) 2CF3-4-Py], [ 5354: 6-Me-5-S (O) 2CF3-4-Py], [5355: 3-CF3-5-S (O) 2CF3-4-Py], [5356: 2-CF3-5-S ( O) 2CF3-4-Py], [5357: 6-CF3-5-S (O) 2CF3-4-Py], [5358: 3-CN-5-S (O) 2CF3-4-Py], [ 5359: 2-CN-5-S (O) 2CF3-4-Py], [5360: 6-CN-5-S (O) 2CF3-4. Py], [5361: 3-OMe-5-S (O) 2CF3-4-Py], [5362: 2-OMe-5-S (O) 2CF3-4-Py], [5363: 6-OMe- 5-S (O) 2CF3-4-Py], [5364: 6-S (O) 2CF3-4-Py], [5365: 3-Cl-6-S (O) 2CF3-4-Py], [ 5366: 2-Cl-6-S (O) 2CF3-4-Py], [5367: 5-Cl-6-S (O) 2CF3-4-Py], [5368: 3-Me-6-S ( O) 2CF3-4-Py], [5369: 2-Me-6-S (O) 2CF3-4-Py], [5370: 5-Me-6-S (O) 2CF3-4-Py], [ 5371: 3-CF3-6-S (O) 2CF3-4-Py], [5372: 2-CF3-6-S (O) 2CF3 -4-Py], [5373: 5-CF3-6-S (O) 2CF3-4-Py], [5374: 3-CN-6-S (O) 2CF3-4-Py], [5375: 2]. -CN-6-S (O) 2CF3-4-Py], [5376: 5-CN-6-S (O) 2CF3-4-Py], [5377: 3-OMe-6-S (O) 2CF3 -4-Py], [5378: 2-OMe-6-S (O) 2CF3-4-Py], [5379: 5-OMe-6-S (O) 2CF3-4-Py], [5380: 3 -CN-4-Py], [5381: 2-Cl-3-CN-4-Py], [5342: 5-Cl-3-CN-4-Py], [5383: 6-Cl-3-CN -4-Py], [5384: 2-Me-3-CN-4-Py], [5385: 5-Me-3-CN-4-Py] [5386: 6-Me-3-CN-4-Py], [5387: 2-CF3-3-CN-4-Py], [5388: 5-CF3-3-CN-4-Py], [5389 : 6-CF3-3-CN-4-Py], [5390: 2-CN-3-CN-4-Py], [5391: 5-CN-3-CN-4-Py], [5392: 6 -CN-3-CN-4-Py], [5393: 2-OMe-3-CN-4-Py], [5394: 5-OMe-3-CN-4-Py], [5395: 6-OMe -3-CN-4-Py], [5396: 2-CN-4-Py], [5397: 3-Cl-2-CN-4-Py], [5398: 5-Cl-2-CN-4 -Py], [5399: 6-Cl-2-CN-4-Py], [5400: 3-Me-2-CN-4-Py],
[5401:5−Me−2−CN−4−Py]、[5402:6−Me−2−CN−4−Py]、[5403:3−CF3−2−CN−4−Py]、[5404:5−CF3−2−CN−4−Py]、[5405:6−CF3−2−CN−4−Py]、[5406:3−CN−2−CN−4−Py]、[5407:5−CN−2−CN−4−Py]、[5408:6−CN−2−CN−4−Py]、[5409:3−OMe−2−CN−4−Py]、[5410:5−OMe−2−CN−4−Py]、[5411:6−OMe−2−CN−4−Py]、[5412:5−CN−4−Py]、[5413:3−Cl−5−CN−4−Py]、[5414:2−Cl−5−CN−4−Py]、[5415:6−Cl−5−CN−4−Py]、[5416:3−Me−5−CN−4−Py]、[5417:2−Me−5−CN−4−Py]、[5418:6−Me−5−CN−4−Py]、[5419:3−CF3−5−CN−4−Py]、[5420:2−CF3−5−CN−4−Py]、[5421:6−CF3−5−CN−4−Py]、[5422:3−CN−5−CN−4−Py]、[5423:2−CN−5−CN−4−Py]、[5424:6−CN−5−CN−4−Py]、[5425:3−OMe−5−CN−4−Py]、[5426:2−OMe−5−CN−4−Py]、[5427:6−OMe−5−CN−4−Py]、[5428:6−CN−4−Py]、[5429:3−Cl−6−CN−4−Py]、[5430:2−Cl−6−CN−4−Py]、[5431:5−Cl−6−CN−4−Py]、[5432:3−Me−6−CN−4−Py]、[5433:2−Me−6−CN−4−Py]、[5434:5−Me−6−CN−4−Py]、[5435:3−CF3−6−CN−4−Py]、[5436:2−CF3−6−CN−4−Py]、[5437:5−CF3−6−CN−4−Py]、[5438:3−CN−6−CN−4−Py]、[5439:2−CN−6−CN−4−Py]、[5440:5−CN−6−CN−4−Py]、[5441:3−OMe−6−CN−4−Py]、[5442:2−OMe−6−CN−4−Py]、[5443:5−OMe−6−CN−4−Py]、[5444:3−COOMe−4−Py]、[5445:2−Cl−3−COOMe−4−Py]、[5446:5−Cl−3−COOMe−4−Py]、[5447:6−Cl−3−COOMe−4−Py]、[5448:2−Me−3−COOMe−4−Py]、[5449:5−Me−3−COOMe−4−Py]、[5450:6−Me−3−COOMe−4−Py]、[5451:2−CF3−3−COOMe−4−Py]、[5452:5−CF3−3−COOMe−4−Py]、[5453:6−CF3−3−COOMe−4−Py]、[5454:2−CN−3−COOMe−4−Py]、[5455:5−CN−3−COOMe−4−Py]、[5456:6−CN−3−COOMe−4−Py]、[5457:2−OMe−3−COOMe−4−Py]、[5458:5−OMe−3−COOMe−4−Py]、[5459:6−OMe−3−COOMe−4−Py]、[5460:2−COOMe−4−Py]、[5461:3−Cl−2−COOMe−4−Py]、[5462:5−Cl−2−COOMe−4−Py]、[5463:6−Cl−2−COOMe−4−Py]、[5464:3−Me−2−COOMe−4−Py]、[5465:5−Me−2−COOMe−4−Py]、[5466:6−Me−2−COOMe−4−Py]、[5467:3−CF3−2−COOMe−4−Py]、[5468:5−CF3−2−COOMe−4−Py]、[5469:6−CF3−2−COOMe−4−Py]、[5470:3−CN−2−COOMe−4−Py]、[5471:5−CN−2−COOMe−4−Py]、[5472:6−CN−2−COOMe−4−Py]、[5473:3−OMe−2−COOMe−4−Py]、[5474:5−OMe−2−COOMe−4−Py]、[5475:6−OMe−2−COOMe−4−Py]、[5476:5−COOMe−4−Py]、[5477:3−Cl−5−COOMe−4−Py]、[5478:2−Cl−5−COOMe−4−Py]、[5479:6−Cl−5−COOMe−4−Py]、[5480:3−Me−5−COOMe−4−Py]、[5481:2−Me−5−COOMe−4−Py]、[5482:6−Me−5−COOMe−4−Py]、[5483:3−CF3−5−COOMe−4−Py]、[5484:2−CF3−5−COOMe−4−Py]、[5485:6−CF3−5−COOMe−4−Py]、[5486:3−CN−5−COOMe−4−Py]、[5487:2−CN−5−COOMe−4−Py]、[5488:6−CN−5−COOMe−4−Py]、[5489:3−OMe−5−COOMe−4−Py]、[5490:2−OMe−5−COOMe−4−Py]、[5491:6−OMe−5−COOMe−4−Py]、[5492:6−COOMe−4−Py]、[5493:3−Cl−6−COOMe−4−Py]、[5494:2−Cl−6−COOMe−4−Py]、[5495:5−Cl−6−COOMe−4−Py]、[5496:3−Me−6−COOMe−4−Py]、[5497:2−Me−6−COOMe−4−Py]、[5498:5−Me−6−COOMe−4−Py]、[5499:3−CF3−6−COOMe−4−Py]、[5500:2−CF3−6−COOMe−4−Py]、 [5401: 5-Me-2-CN-4-Py], [5402: 6-Me-2-CN-4-Py], [5403: 3-CF3-2-CN-4-Py], [5404 : 5-CF3-2-CN-4-Py], [5405: 6-CF3-2-CN-4-Py], [5406: 3-CN-2-CN-4-Py], [5407: 5 -CN-2-CN-4-Py], [5408: 6-CN-2-CN-4-Py], [5409: 3-OMe-2-CN-4-Py], [5410: 5-OMe -2-CN-4-Py], [5411: 6-OMe-2-CN-4-Py], [5412: 5-CN-4-Py], [5413: 3-Cl-5-CN-4 -Py], [5414: 2-Cl-5-CN-4-Py], [5415: 6-Cl-5-CN-4-Py], [5 16: 3-Me-5-CN-4-Py], [5417: 2-Me-5-CN-4-Py], [5418: 6-Me-5-CN-4-Py], [5419: 3-CF3-5-CN-4-Py], [5420: 2-CF3-5-CN-4-Py], [5421: 6-CF3-5-CN-4-Py], [5422: 3- CN-5-CN-4-Py], [5423: 2-CN-5-CN-4-Py], [5424: 6-CN-5-CN-4-Py], [5425: 3-OMe- 5-CN-4-Py], [5426: 2-OMe-5-CN-4-Py], [5427: 6-OMe-5-CN-4-Py], [5428: 6-CN-4- Py], [5429: 3-Cl-6-CN-4-Py], [5430: 2-Cl-6-CN-4-Py], [543 : 5-Cl-6-CN-4-Py], [5432: 3-Me-6-CN-4-Py], [5433: 2-Me-6-CN-4-Py], [5434: 5 -Me-6-CN-4-Py], [5435: 3-CF3-6-CN-4-Py], [5436: 2-CF3-6-CN-4-Py], [5437: 5-CF3 -6-CN-4-Py], [5438: 3-CN-6-CN-4-Py], [5439: 2-CN-6-CN-4-Py], [5440: 5-CN-6. -CN-4-Py], [5441: 3-OMe-6-CN-4-Py], [5442: 2-OMe-6-CN-4-Py], [5443: 5-OMe-6-CN. -4-Py], [5444: 3-COOMe-4-Py], [5445: 2-Cl-3-COOMe-4-Py], [ 5446: 5-Cl-3-COOMe-4-Py], [5447: 6-Cl-3-COOMe-4-Py], [5448: 2-Me-3-COOMe-4-Py], [5449: 5-Me-3-COOMe-4-Py], [5450: 6-Me-3-COOMe-4-Py], [5451: 2-CF3-3-COOMe-4-Py], [5452: 5- CF3-3-COOMe-4-Py], [5453: 6-CF3-3-COOMe-4-Py], [5454: 2-CN-3-COOMe-4-Py], [5455: 5-CN- 3-COOMe-4-Py], [5456: 6-CN-3-COOMe-4-Py], [5457: 2-OMe-3-COOMe-4-Py], [5458: 5-OMe-3- COOMe-4-Py], [545 : 6-OMe-3-COOMe-4-Py], [5460: 2-COOMe-4-Py], [5461: 3-Cl-2-COOMe-4-Py], [5462: 5-Cl-2] -COOMe-4-Py], [5463: 6-Cl-2-COOMe-4-Py], [5464: 3-Me-2-COOMe-4-Py], [5465: 5-Me-2-COOMe -4-Py], [5466: 6-Me-2-COOMe-4-Py], [5467: 3-CF3-2-COOMe-4-Py], [5468: 5-CF3-2-COOMe-4 -Py], [5469: 6-CF3-2-COOMe-4-Py], [5470: 3-CN-2-COOMe-4-Py], [5471: 5-CN-2-COOMe-4-Py ], [5472: 6-CN-2- OOMe-4-Py], [5473: 3-OMe-2-COOMe-4-Py], [5474: 5-OMe-2-COOMe-4-Py], [5475: 6-OMe-2-COOMe- 4-Py], [5476: 5-COOMe-4-Py], [5477: 3-Cl-5-COOMe-4-Py], [5478: 2-Cl-5-COOMe-4-Py], [ 5479: 6-Cl-5-COOMe-4-Py], [5480: 3-Me-5-COOMe-4-Py], [5481: 2-Me-5-COOMe-4-Py], [5482: 6-Me-5-COOMe-4-Py], [5483: 3-CF3-5-COOMe-4-Py], [5484: 2-CF3-5-COOMe-4-Py], [5485: 6- CF3-5-COOMe-4- Py], [5486: 3-CN-5-COOMe-4-Py], [5487: 2-CN-5-COOMe-4-Py], [5488: 6-CN-5-COOMe-4-Py] [5489: 3-OMe-5-COOMe-4-Py], [5490: 2-OMe-5-COOMe-4-Py], [5491: 6-OMe-5-COOMe-4-Py], [ 5492: 6-COOMe-4-Py], [5493: 3-Cl-6-COOMe-4-Py], [5494: 2-Cl-6-COOMe-4-Py], [5495: 5-Cl- 6-COOMe-4-Py], [5496: 3-Me-6-COOMe-4-Py], [5497: 2-Me-6-COOMe-4-Py], [5498: 5-Me-6 COOMe-4-Py], [5499: -CF3-6-COOMe-4-Py], [5500: 2-CF3-6-COOMe-4-Py],
[5501:5−CF3−6−COOMe−4−Py]、[5502:3−CN−6−COOMe−4−Py]、[5503:2−CN−6−COOMe−4−Py]、[5504:5−CN−6−COOMe−4−Py]、[5505:3−OMe−6−COOMe−4−Py]、[5506:2−OMe−6−COOMe−4−Py]、[5507:5−OMe−6−COOMe−4−Py]、[5508:3−NO2−4−Py]、[5509:2−Cl−3−NO2−4−Py]、[5510:5−Cl−3−NO2−4−Py]、[5511:6−Cl−3−NO2−4−Py]、[5512:2−Me−3−NO2−4−Py]、[5513:5−Me−3−NO2−4−Py]、[5514:6−Me−3−NO2−4−Py]、[5515:2−CF3−3−NO2−4−Py]、[5516:5−CF3−3−NO2−4−Py]、[5517:6−CF3−3−NO2−4−Py]、[5518:2−CN−3−NO2−4−Py]、[5519:5−CN−3−NO2−4−Py]、[5520:6−CN−3−NO2−4−Py]、[5521:2−OMe−3−NO2−4−Py]、[5522:5−OMe−3−NO2−4−Py]、[5523:6−OMe−3−NO2−4−Py]、[5524:2−NO2−4−Py]、[5525:3−Cl−2−NO2−4−Py]、[5526:5−Cl−2−NO2−4−Py]、[5527:6−Cl−2−NO2−4−Py]、[5528:3−Me−2−NO2−4−Py]、[5529:5−Me−2−NO2−4−Py]、[5530:6−Me−2−NO2−4−Py]、[5531:3−CF3−2−NO2−4−Py]、[5532:5−CF3−2−NO2−4−Py]、[5533:6−CF3−2−NO2−4−Py]、[5534:3−CN−2−NO2−4−Py]、[5535:5−CN−2−NO2−4−Py]、[5536:6−CN−2−NO2−4−Py]、[5537:3−OMe−2−NO2−4−Py]、[5538:5−OMe−2−NO2−4−Py]、[5539:6−OMe−2−NO2−4−Py]、[5540:5−NO2−4−Py]、[5541:3−Cl−5−NO2−4−Py]、[5542:2−Cl−5−NO2−4−Py]、[5543:6−Cl−5−NO2−4−Py]、[5544:3−Me−5−NO2−4−Py]、[5545:2−Me−5−NO2−4−Py]、[5546:6−Me−5−NO2−4−Py]、[5547:3−CF3−5−NO2−4−Py]、[5548:2−CF3−5−NO2−4−Py]、[5549:6−CF3−5−NO2−4−Py]、[5550:3−CN−5−NO2−4−Py]、[5551:2−CN−5−NO2−4−Py]、[5552:6−CN−5−NO2−4−Py]、[5553:3−OMe−5−NO2−4−Py]、[5554:2−OMe−5−NO2−4−Py]、[5555:6−OMe−5−NO2−4−Py]、[5556:6−NO2−4−Py]、[5557:3−Cl−6−NO2−4−Py]、[5558:2−Cl−6−NO2−4−Py]、[5559:5−Cl−6−NO2−4−Py]、[5560:3−Me−6−NO2−4−Py]、[5561:2−Me−6−NO2−4−Py]、[5562:5−Me−6−NO2−4−Py]、[5563:3−CF3−6−NO2−4−Py]、[5564:2−CF3−6−NO2−4−Py]、[5565:5−CF3−6−NO2−4−Py]、[5566:3−CN−6−NO2−4−Py]、[5567:2−CN−6−NO2−4−Py]、[5568:5−CN−6−NO2−4−Py]、[5569:3−OMe−6−NO2−4−Py]、[5570:2−OMe−6−NO2−4−Py]、[5571:5−OMe−6−NO2−4−Py]、[5572:3−NH2−4−Py]、[5573:2−Cl−3−NH2−4−Py]、[5574:5−Cl−3−NH2−4−Py]、[5575:6−Cl−3−NH2−4−Py]、[5576:2−Me−3−NH2−4−Py]、[5577:5−Me−3−NH2−4−Py]、[5578:6−Me−3−NH2−4−Py]、[5579:2−CF3−3−NH2−4−Py]、[5580:5−CF3−3−NH2−4−Py]、[5581:6−CF3−3−NH2−4−Py]、[5582:2−CN−3−NH2−4−Py]、[5583:5−CN−3−NH2−4−Py]、[5584:6−CN−3−NH2−4−Py]、[5585:2−OMe−3−NH2−4−Py]、[5586:5−OMe−3−NH2−4−Py]、[5587:6−OMe−3−NH2−4−Py]、[5588:2−NH2−4−Py]、[5589:3−Cl−2−NH2−4−Py]、[5590:5−Cl−2−NH2−4−Py]、[5591:6−Cl−2−NH2−4−Py]、[5592:3−Me−2−NH2−4−Py]、[5593:5−Me−2−NH2−4−Py]、[5594:6−Me−2−NH2−4−Py]、[5595:3−CF3−2−NH2−4−Py]、[5596:5−CF3−2−NH2−4−Py]、[5597:6−CF3−2−NH2−4−Py]、[5598:3−CN−2−NH2−4−Py]、[5599:5−CN−2−NH2−4−Py]、[5600:6−CN−2−NH2−4−Py]、 [5501: 5-CF3-6-COOMe-4-Py], [5502: 3-CN-6-COOMe-4-Py], [5503: 2-CN-6-COOMe-4-Py], [5504 : 5-CN-6-COOMe-4-Py], [5505: 3-OMe-6-COOMe-4-Py], [5506: 2-OMe-6-COOMe-4-Py], [5507: 5 -OMe-6-COOMe-4-Py], [5508: 3-NO2-4-Py], [5509: 2-Cl-3-NO2-4-Py], [5510: 5-Cl-3-NO2 -4-Py], [5511: 6-Cl-3-NO2-4-Py], [5512: 2-Me-3-NO2-4-Py], [5513: 5-Me-3-NO2-4. -Py], [5514: 6-Me-3-NO2-4-Py [5515: 2-CF3-3-NO2-4-Py], [5516: 5-CF3-3-NO2-4-Py], [5517: 6-CF3-3-NO2-4-Py], [ 5518: 2-CN-3-NO2-4-Py], [5519: 5-CN-3-NO2-4-Py], [5520: 6-CN-3-NO2-4-Py], [5521: 2-OMe-3-NO2-4-Py], [5522: 5-OMe-3-NO2-4-Py], [5523: 6-OMe-3-NO2-4-Py], [5524: 2- NO2-4-Py], [5525: 3-Cl-2-NO2-4-Py], [5526: 5-Cl-2-NO2-4-Py], [5527: 6-Cl-2-NO2- 4-Py], [5528: 3-Me-2-NO2-4-Py], [5529: 5- e-2-NO2-4-Py], [5530: 6-Me-2-NO2-4-Py], [5531: 3-CF3-2-NO2-4-Py], [5532: 5-CF3- 2-NO2-4-Py], [5533: 6-CF3-2-NO2-4-Py], [5534: 3-CN-2-NO2-4-Py], [5535: 5-CN-2- NO2-4-Py], [5536: 6-CN-2-NO2-4-Py], [5537: 3-OMe-2-NO2-4-Py], [5538: 5-OMe-2-NO2- 4-Py], [5539: 6-OMe-2-NO2-4-Py], [5540: 5-NO2-4-Py], [5541: 3-Cl-5-NO2-4-Py], [ 5542: 2-Cl-5-NO2-4-Py], [5543: 6-Cl-5-NO2-4- Py], [5544: 3-Me-5-NO2-4-Py], [5545: 2-Me-5-NO2-4-Py], [5546: 6-Me-5-NO2-4-Py] [5547: 3-CF3-5-NO2-4-Py], [5548: 2-CF3-5-NO2-4-Py], [5549: 6-CF3-5-NO2-4-Py], [ 5550: 3-CN-5-NO2-4-Py], [5551: 2-CN-5-NO2-4-Py], [5552: 6-CN-5-NO2-4-Py], [5553: 3-OMe-5-NO2-4-Py], [5554: 2-OMe-5-NO2-4-Py], [5555: 6-OMe-5-NO2-4-Py], [5556: 6- NO2-4-Py], [5557: 3-Cl-6-NO2-4-Py], [5558: -Cl-6-NO2-4-Py], [5559: 5-Cl-6-NO2-4-Py], [5560: 3-Me-6-NO2-4-Py], [5561: 2-Me -6-NO2-4-Py], [5562: 5-Me-6-NO2-4-Py], [5563: 3-CF3-6-NO2-4-Py], [5564: 2-CF3-6. -NO2-4-Py], [5565: 5-CF3-6-NO2-4-Py], [5566: 3-CN-6-NO2-4-Py], [5567: 2-CN-6-NO2 -4-Py], [5568: 5-CN-6-NO2-4-Py], [5569: 3-OMe-6-NO2-4-Py], [5570: 2-OMe-6-NO2-4 -Py], [5571: 5-OMe-6-NO2-4-Py], [5572: 3-NH2 4-Py], [5573: 2-Cl-3-NH2-4-Py], [5574: 5-Cl-3-NH2-4-Py], [5575: 6-Cl-3-NH2-4- Py], [5576: 2-Me-3-NH2-4-Py], [5577: 5-Me-3-NH2-4-Py], [5578: 6-Me-3-NH2-4-Py] [5579: 2-CF3-3-NH2-4-Py], [5580: 5-CF3-3-NH2-4-Py], [5581: 6-CF3-3-NH2-4-Py], [ 5582: 2-CN-3-NH2-4-Py], [5583: 5-CN-3-NH2-4-Py], [5584: 6-CN-3-NH2-4-Py], [5585: 2-OMe-3-NH2-4-Py], [5586: 5-OMe-3-NH2-4-Py], [5587: 6-OMe-3-NH2-4-Py], [5588: 2-NH2-4-Py], [5589: 3-Cl-2-NH2-4-Py], [5590: 5-Cl -2-NH2-4-Py], [5591: 6-Cl-2-NH2-4-Py], [5592: 3-Me-2-NH2-4-Py], [5593: 5-Me-2 -NH2-4-Py], [5594: 6-Me-2-NH2-4-Py], [5595: 3-CF3-2-NH2-4-Py], [5596: 5-CF3-2-NH2 -4-Py], [5597: 6-CF3-2-NH2-4-Py], [5598: 3-CN-2-NH2-4-Py], [5599: 5-CN-2-NH2-4 -Py], [5600: 6-CN-2-NH2-4-Py],
[5601:3−OMe−2−NH2−4−Py]、[5602:5−OMe−2−NH2−4−Py]、[5603:6−OMe−2−NH2−4−Py]、[5604:5−NH2−4−Py]、[5605:3−Cl−5−NH2−4−Py]、[5606:2−Cl−5−NH2−4−Py]、[5607:6−Cl−5−NH2−4−Py]、[5608:3−Me−5−NH2−4−Py]、[5609:2−Me−5−NH2−4−Py]、[5610:6−Me−5−NH2−4−Py]、[5611:3−CF3−5−NH2−4−Py]、[5612:2−CF3−5−NH2−4−Py]、[5613:6−CF3−5−NH2−4−Py]、[5614:3−CN−5−NH2−4−Py]、[5615:2−CN−5−NH2−4−Py]、[5616:6−CN−5−NH2−4−Py]、[5617:3−OMe−5−NH2−4−Py]、[5618:2−OMe−5−NH2−4−Py]、[5619:6−OMe−5−NH2−4−Py]、[5620:6−NH2−4−Py]、[5621:3−Cl−6−NH2−4−Py]、[5622:2−Cl−6−NH2−4−Py]、[5623:5−Cl−6−NH2−4−Py]、[5624:3−Me−6−NH2−4−Py]、[5625:2−Me−6−NH2−4−Py]、[5626:5−Me−6−NH2−4−Py]、[5627:3−CF3−6−NH2−4−Py]、[5628:2−CF3−6−NH2−4−Py]、[5629:5−CF3−6−NH2−4−Py]、[5630:3−CN−6−NH2−4−Py]、[5631:2−CN−6−NH2−4−Py]、[5632:5−CN−6−NH2−4−Py]、[5633:3−OMe−6−NH2−4−Py]、[5634:2−OMe−6−NH2−4−Py]、[5635:5−OMe−6−NH2−4−Py]、[5636:3−NHMe−4−Py]、[5637:2−Cl−3−NHMe−4−Py]、[5638:5−Cl−3−NHMe−4−Py]、[5639:6−Cl−3−NHMe−4−Py]、[5640:2−Me−3−NHMe−4−Py]、[5641:5−Me−3−NHMe−4−Py]、[5642:6−Me−3−NHMe−4−Py]、[5643:2−CF3−3−NHMe−4−Py]、[5644:5−CF3−3−NHMe−4−Py]、[5645:6−CF3−3−NHMe−4−Py]、[5646:2−CN−3−NHMe−4−Py]、[5647:5−CN−3−NHMe−4−Py]、[5648:6−CN−3−NHMe−4−Py]、[5649:2−OMe−3−NHMe−4−Py]、[5650:5−OMe−3−NHMe−4−Py]、[5651:6−OMe−3−NHMe−4−Py]、[5652:2−NHMe−4−Py]、[5653:3−Cl−2−NHMe−4−Py]、[5654:5−Cl−2−NHMe−4−Py]、[5655:6−Cl−2−NHMe−4−Py]、[5656:3−Me−2−NHMe−4−Py]、[5657:5−Me−2−NHMe−4−Py]、[5658:6−Me−2−NHMe−4−Py]、[5659:3−CF3−2−NHMe−4−Py]、[5660:5−CF3−2−NHMe−4−Py]、[5661:6−CF3−2−NHMe−4−Py]、[5662:3−CN−2−NHMe−4−Py]、[5663:5−CN−2−NHMe−4−Py]、[5664:6−CN−2−NHMe−4−Py]、[5665:3−OMe−2−NHMe−4−Py]、[5666:5−OMe−2−NHMe−4−Py]、[5667:6−OMe−2−NHMe−4−Py]、[5668:5−NHMe−4−Py]、[5669:3−Cl−5−NHMe−4−Py]、[5670:2−Cl−5−NHMe−4−Py]、[5671:6−Cl−5−NHMe−4−Py]、[5672:3−Me−5−NHMe−4−Py]、[5673:2−Me−5−NHMe−4−Py]、[5674:6−Me−5−NHMe−4−Py]、[5675:3−CF3−5−NHMe−4−Py]、[5676:2−CF3−5−NHMe−4−Py]、[5677:6−CF3−5−NHMe−4−Py]、[5678:3−CN−5−NHMe−4−Py]、[5679:2−CN−5−NHMe−4−Py]、[5680:6−CN−5−NHMe−4−Py]、[5681:3−OMe−5−NHMe−4−Py]、[5682:2−OMe−5−NHMe−4−Py]、[5683:6−OMe−5−NHMe−4−Py]、[5684:6−NHMe−4−Py]、[5685:3−Cl−6−NHMe−4−Py]、[5686:2−Cl−6−NHMe−4−Py]、[5687:5−Cl−6−NHMe−4−Py]、[5688:3−Me−6−NHMe−4−Py]、[5689:2−Me−6−NHMe−4−Py]、[5690:5−Me−6−NHMe−4−Py]、[5691:3−CF3−6−NHMe−4−Py]、[5692:2−CF3−6−NHMe−4−Py]、[5693:5−CF3−6−NHMe−4−Py]、[5694:3−CN−6−NHMe−4−Py]、[5695:2−CN−6−NHMe−4−Py]、[5696:5−CN−6−NHMe−4−Py]、[5697:3−OMe−6−NHMe−4−Py]、[5698:2−OMe−6−NHMe−4−Py]、[5699:5−OMe−6−NHMe−4−Py]、[5700:3−NMe2−4−Py]、 [5601: 3-OMe-2-NH2-4-Py], [5602: 5-OMe-2-NH2-4-Py], [5603: 6-OMe-2-NH2-4-Py], [5604 : 5-NH2-4-Py], [5605: 3-Cl-5-NH2-4-Py], [5606: 2-Cl-5-NH2-4-Py], [5607: 6-Cl-5 -NH2-4-Py], [5608: 3-Me-5-NH2-4-Py], [5609: 2-Me-5-NH2-4-Py], [5610: 6-Me-5-NH2 -4-Py], [5611: 3-CF3-5-NH2-4-Py], [5612: 2-CF3-5-NH2-4-Py], [5613: 6-CF3-5-NH2-4 -Py], [5614: 3-CN-5-NH2-4-Py], [5615: 2-CN 5-NH2-4-Py], [5616: 6-CN-5-NH2-4-Py], [5617: 3-OMe-5-NH2-4-Py], [5618: 2-OMe-5 NH2-4-Py], [5619: 6-OMe-5-NH2-4-Py], [5620: 6-NH2-4-Py], [5621: 3-Cl-6-NH2-4-Py] [5622: 2-Cl-6-NH2-4-Py], [5623: 5-Cl-6-NH2-4-Py], [5624: 3-Me-6-NH2-4-Py], [ 5625: 2-Me-6-NH2-4-Py], [5626: 5-Me-6-NH2-4-Py], [5627: 3-CF3-6-NH2-4-Py], [5628: 2-CF3-6-NH2-4-Py], [5629: 5-CF3-6-NH2-4-P ], [5630: 3-CN-6-NH2-4-Py], [5631: 2-CN-6-NH2-4-Py], [5632: 5-CN-6-NH2-4-Py], [5633: 3-OMe-6-NH2-4-Py], [5634: 2-OMe-6-NH2-4-Py], [5635: 5-OMe-6-NH2-4-Py], [5636 : 3-NHMe-4-Py], [5637: 2-Cl-3-NHMe-4-Py], [5638: 5-Cl-3-NHMe-4-Py], [5639: 6-Cl-3 -NHMe-4-Py], [5640: 2-Me-3-NHMe-4-Py], [5641: 5-Me-3-NHMe-4-Py], [5642: 6-Me-3-NHMe -4-Py], [5643: 2-CF3-3-NHMe-4-Py], [5 644: 5-CF3-3-NHMe-4-Py], [5645: 6-CF3-3-NHMe-4-Py], [5646: 2-CN-3-NHMe-4-Py], [5647: 5-CN-3-NHMe-4-Py], [5648: 6-CN-3-NHMe-4-Py], [5649: 2-OMe-3-NHMe-4-Py], [5650: 5- OMe-3-NHMe-4-Py], [5651: 6-OMe-3-NHMe-4-Py], [5652: 2-NHMe-4-Py], [5653: 3-Cl-2-NHMe- 4-Py], [5654: 5-Cl-2-NHMe-4-Py], [5655: 6-Cl-2-NHMe-4-Py], [5656: 3-Me-2-NHMe-4- Py], [5657: 5-Me-2-NHMe-4-Py] [5658: 6-Me-2-NHMe-4-Py], [5659: 3-CF3-2-NHMe-4-Py], [5660: 5-CF3-2-NHMe-4-Py], [5661 : 6-CF3-2-NHMe-4-Py], [5662: 3-CN-2-NHMe-4-Py], [5663: 5-CN-2-NHMe-4-Py], [5664: 6 -CN-2-NHMe-4-Py], [5665: 3-OMe-2-NHMe-4-Py], [5666: 5-OMe-2-NHMe-4-Py], [5667: 6-OMe -2-NHMe-4-Py], [5668: 5-NHMe-4-Py], [5669: 3-Cl-5-NHMe-4-Py], [5670: 2-Cl-5-NHMe-4 -Py], [5671: 6-Cl-5-NHMe-4 Py], [5672: 3-Me-5-NHMe-4-Py], [5673: 2-Me-5-NHMe-4-Py], [5674: 6-Me-5-NHMe-4-Py] [5675: 3-CF3-5-NHMe-4-Py], [5676: 2-CF3-5-NHMe-4-Py], [5777: 6-CF3-5-NHMe-4-Py], [ 5678: 3-CN-5-NHMe-4-Py], [5679: 2-CN-5-NHMe-4-Py], [5680: 6-CN-5-NHMe-4-Py], [5681: 3-OMe-5-NHMe-4-Py], [5682: 2-OMe-5-NHMe-4-Py], [5683: 6-OMe-5-NHMe-4-Py], [5684: 6- NHMe-4-Py], [5585: 3-Cl-6-NHM e-4-Py], [5686: 2-Cl-6-NHMe-4-Py], [5687: 5-Cl-6-NHMe-4-Py], [5688: 3-Me-6-NHMe- 4-Py], [5629: 2-Me-6-NHMe-4-Py], [5690: 5-Me-6-NHMe-4-Py], [5691: 3-CF3-6-NHMe-4- Py], [5692: 2-CF3-6-NHMe-4-Py], [5663: 5-CF3-6-NHMe-4-Py], [5694: 3-CN-6-NHMe-4-Py] [5695: 2-CN-6-NHMe-4-Py], [5696: 5-CN-6-NHMe-4-Py], [5697: 3-OMe-6-NHMe-4-Py], [ 5698: 2-OMe-6-NHMe-4-Py], [5699: 5- Me-6-NHMe-4-Py], [5700: 3-NMe2-4-Py],
[5701:2−Cl−3−NMe2−4−Py]、[5702:5−Cl−3−NMe2−4−Py]、[5703:6−Cl−3−NMe2−4−Py]、[5704:2−Me−3−NMe2−4−Py]、[5705:5−Me−3−NMe2−4−Py]、[5706:6−Me−3−NMe2−4−Py]、[5707:2−CF3−3−NMe2−4−Py]、[5708:5−CF3−3−NMe2−4−Py]、[5709:6−CF3−3−NMe2−4−Py]、[5710:2−CN−3−NMe2−4−Py]、[5711:5−CN−3−NMe2−4−Py]、[5712:6−CN−3−NMe2−4−Py]、[5713:2−OMe−3−NMe2−4−Py]、[5714:5−OMe−3−NMe2−4−Py]、[5715:6−OMe−3−NMe2−4−Py]、[5716:4−NMe2−4−Py]、[5717:3−Cl−4−NMe2−4−Py]、[5718:5−Cl−4−NMe2−4−Py]、[5719:6−Cl−4−NMe2−4−Py]、[5720:3−Me−4−NMe2−4−Py]、[5721:5−Me−4−NMe2−4−Py]、[5722:6−Me−4−NMe2−4−Py]、[5723:3−CF3−4−NMe2−4−Py]、[5724:5−CF3−4−NMe2−4−Py]、[5725:6−CF3−4−NMe2−4−Py]、[5726:3−CN−4−NMe2−4−Py]、[5727:5−CN−4−NMe2−4−Py]、[5728:6−CN−4−NMe2−4−Py]、[5729:3−OMe−4−NMe2−4−Py]、[5730:5−OMe−4−NMe2−4−Py]、[5731:6−OMe−4−NMe2−4−Py]、[5732:5−NMe2−4−Py]、[5733:3−Cl−5−NMe2−4−Py]、[5734:2−Cl−5−NMe2−4−Py]、[5735:6−Cl−5−NMe2−4−Py]、[5736:3−Me−5−NMe2−4−Py]、[5737:2−Me−5−NMe2−4−Py]、[5738:6−Me−5−NMe2−4−Py]、[5739:3−CF3−5−NMe2−4−Py]、[5740:2−CF3−5−NMe2−4−Py]、[5741:6−CF3−5−NMe2−4−Py]、[5742:3−CN−5−NMe2−4−Py]、[5743:2−CN−5−NMe2−4−Py]、[5744:6−CN−5−NMe2−4−Py]、[5745:3−OMe−5−NMe2−4−Py]、[5746:2−OMe−5−NMe2−4−Py]、[5747:6−OMe−5−NMe2−4−Py]、[5748:6−NMe2−4−Py]、[5749:3−Cl−6−NMe2−4−Py]、[5750:2−Cl−6−NMe2−4−Py]、[5751:5−Cl−6−NMe2−4−Py]、[5752:3−Me−6−NMe2−4−Py]、[5753:2−Me−6−NMe2−4−Py]、[5754:5−Me−6−NMe2−4−Py]、[5755:3−CF3−6−NMe2−4−Py]、[5756:2−CF3−6−NMe2−4−Py]、[5757:5−CF3−6−NMe2−4−Py]、[5758:3−CN−6−NMe2−4−Py]、[5759:2−CN−6−NMe2−4−Py]、[5760:5−CN−6−NMe2−4−Py]、[5761:3−OMe−6−NMe2−4−Py]、[5762:2−OMe−6−NMe2−4−Py]、[5763:5−OMe−6−NMe2−4−Py]、[5764:3−ACNH−4−Py]、[5765:2−Cl−3−ACNH−4−Py]、[5766:5−Cl−3−ACNH−4−Py]、[5767:6−Cl−3−ACNH−4−Py]、[5768:2−Me−3−ACNH−4−Py]、[5769:5−Me−3−ACNH−4−Py]、[5770:6−Me−3−ACNH−4−Py]、[5771:2−CF3−3−ACNH−4−Py]、[5772:5−CF3−3−ACNH−4−Py]、[5773:6−CF3−3−ACNH−4−Py]、[5774:2−CN−3−ACNH−4−Py]、[5775:5−CN−3−ACNH−4−Py]、[5776:6−CN−3−ACNH−4−Py]、[5777:2−OMe−3−ACNH−4−Py]、[5778:5−OMe−3−ACNH−4−Py]、[5779:6−OMe−3−ACNH−4−Py]、[5780:2−ACNH−4−Py]、[5781:3−Cl−2−ACNH−4−Py]、[5782:5−Cl−2−ACNH−4−Py]、[5783:6−Cl−2−ACNH−4−Py]、[5784:3−Me−2−ACNH−4−Py]、[5785:5−Me−2−ACNH−4−Py]、[5786:6−Me−2−ACNH−4−Py]、[5787:3−CF3−2−ACNH−4−Py]、[5788:5−CF3−2−ACNH−4−Py]、[5789:6−CF3−2−ACNH−4−Py]、[5790:3−CN−2−ACNH−4−Py]、[5791:5−CN−2−ACNH−4−Py]、[5792:6−CN−2−ACNH−4−Py]、[5793:3−OMe−2−ACNH−4−Py]、[5794:5−OMe−2−ACNH−4−Py]、[5795:6−OMe−2−ACNH−4−Py]、[5796:5−ACNH−4−Py]、[5797:3−Cl−5−ACNH−4−Py]、[5798:2−Cl−5−ACNH−4−Py]、[5799:6−Cl−5−ACNH−4−Py]、[5800:3−Me−5−ACNH−4−Py] [5701: 2-Cl-3-NMe2-4-Py], [5702: 5-Cl-3-NMe2-4-Py], [5703: 6-Cl-3-NMe2-4-Py], [5704 : 2-Me-3-NMe2-4-Py], [5705: 5-Me-3-NMe2-4-Py], [5706: 6-Me-3-NMe2-4-Py], [5707: 2]. -CF3-3-NMe2-4-Py], [5708: 5-CF3-3-NMe2-4-Py], [5709: 6-CF3-3-NMe2-4-Py], [5710: 2-CN -3-NMe2-4-Py], [5711: 5-CN-3-NMe2-4-Py], [5712: 6-CN-3-NMe2-4-Py], [5713: 2-OMe-3 -NMe2-4-Py], [5714: 5-OMe-3-NMe -4-Py], [5715: 6-OMe-3-NMe2-4-Py], [5716: 4-NMe2-4-Py], [5717: 3-Cl-4-NMe2-4-Py], [5718: 5-Cl-4-NMe2-4-Py], [5719: 6-Cl-4-NMe2-4-Py], [5720: 3-Me-4-NMe2-4-Py], [5721 : 5-Me-4-NMe2-4-Py], [5722: 6-Me-4-NMe2-4-Py], [5723: 3-CF3-4-NMe2-4-Py], [5724: 5. -CF3-4-NMe2-4-Py], [5725: 6-CF3-4-NMe2-4-Py], [5726: 3-CN-4-NMe2-4-Py], [5727: 5-CN -4-NMe2-4-Py], [5728: 6-CN-4-N e2-4-Py], [5729: 3-OMe-4-NMe2-4-Py], [5730: 5-OMe-4-NMe2-4-Py], [5731: 6-OMe-4-NMe2- 4-Py], [5732: 5-NMe2-4-Py], [5733: 3-Cl-5-NMe2-4-Py], [5734: 2-Cl-5-NMe2-4-Py], [ 5735: 6-Cl-5-NMe2-4-Py], [5736: 3-Me-5-NMe2-4-Py], [5737: 2-Me-5-NMe2-4-Py], [5738: 6-Me-5-NMe2-4-Py], [5739: 3-CF3-5-NMe2-4-Py], [5740: 2-CF3-5-NMe2-4-Py], [5741: 6- CF3-5-NMe2-4-Py], [5742: 3-CN- 5-NMe2-4-Py], [5743: 2-CN-5-NMe2-4-Py], [5744: 6-CN-5-NMe2-4-Py], [5745: 3-OMe-5 NMe2-4-Py], [5746: 2-OMe-5-NMe2-4-Py], [5747: 6-OMe-5-NMe2-4-Py], [5748: 6-NMe2-4-Py] [5749: 3-Cl-6-NMe2-4-Py], [5750: 2-Cl-6-NMe2-4-Py], [5751: 5-Cl-6-NMe2-4-Py], [ 5752: 3-Me-6-NMe2-4-Py], [5753: 2-Me-6-NMe2-4-Py], [5754: 5-Me-6-NMe2-4-Py], [5755: 3-CF3-6-NMe2-4-Py], [5756: 2-C 3-6-NMe2-4-Py], [5757: 5-CF3-6-NMe2-4-Py], [5758: 3-CN-6-NMe2-4-Py], [5759: 2-CN- 6-NMe2-4-Py], [5760: 5-CN-6-NMe2-4-Py], [5761: 3-OMe-6-NMe2-4-Py], [5762: 2-OMe-6 NMe2-4-Py], [5763: 5-OMe-6-NMe2-4-Py], [5764: 3-ACNH-4-Py], [5765: 2-Cl-3-ACNH-4-Py] [5766: 5-Cl-3-ACNH-4-Py], [5767: 6-Cl-3-ACNH-4-Py], [5768: 2-Me-3-ACNH-4-Py], [ 5769: 5-Me-3-ACNH-4-Py], [5770: -Me-3-ACNH-4-Py], [5771: 2-CF3-3-ACNH-4-Py], [5772: 5-CF3-3-ACNH-4-Py], [5773: 6-CF3 -3-ACNH-4-Py], [5774: 2-CN-3-ACNH-4-Py], [5775: 5-CN-3-ACNH-4-Py], [5776: 6-CN-3 -ACNH-4-Py], [5777: 2-OMe-3-ACNH-4-Py], [5778: 5-OMe-3-ACNH-4-Py], [5779: 6-OMe-3-ACNH -4-Py], [5780: 2-ACNH-4-Py], [5781: 3-Cl-2-ACNH-4-Py], [5782: 5-Cl-2-ACNH-4-Py], [5783: 6-Cl-2-ACNH-4-Py], [57 84: 3-Me-2-ACNH-4-Py], [5785: 5-Me-2-ACNH-4-Py], [5786: 6-Me-2-ACNH-4-Py], [5787: 3-CF3-2-ACNH-4-Py], [5788: 5-CF3-2-ACNH-4-Py], [5789: 6-CF3-2-ACNH-4-Py], [5790: 3- CN-2-ACNH-4-Py], [5791: 5-CN-2-ACNH-4-Py], [5792: 6-CN-2-ACNH-4-Py], [5793: 3-OMe- 2-ACNH-4-Py], [5794: 5-OMe-2-ACNH-4-Py], [5795: 6-OMe-2-ACNH-4-Py], [5796: 5-ACNH-4- Py], [5797: 3-Cl-5-ACNH-4-Py] [5798: 2-Cl-5-ACNH-4-Py], [5799: 6-Cl-5-ACNH-4-Py], [5800: 3-Me-5-ACNH-4-Py]
[5801:2−Me−5−ACNH−4−Py]、[5802:6−Me−5−ACNH−4−Py]、[5803:3−CF3−5−ACNH−4−Py]、[5804:2−CF3−5−ACNH−4−Py]、[5805:6−CF3−5−ACNH−4−Py]、[5806:3−CN−5−ACNH−4−Py]、[5807:2−CN−5−ACNH−4−Py]、[5808:6−CN−5−ACNH−4−Py]、[5809:3−OMe−5−ACNH−4−Py]、[5810:2−OMe−5−ACNH−4−Py]、[5811:6−OMe−5−ACNH−4−Py]、[5812:6−ACNH−4−Py]、[5813:3−Cl−6−ACNH−4−Py]、[5814:2−Cl−6−ACNH−4−Py]、[5815:5−Cl−6−ACNH−4−Py]、[5816:3−Me−6−ACNH−4−Py]、[5817:2−Me−6−ACNH−4−Py]、[5818:5−Me−6−ACNH−4−Py]、[5819:3−CF3−6−ACNH−4−Py]、[5820:2−CF3−6−ACNH−4−Py]、[5821:5−CF3−6−ACNH−4−Py]、[5822:3−CN−6−ACNH−4−Py]、[5823:2−CN−6−ACNH−4−Py]、[5824:5−CN−6−ACNH−4−Py]、[5825:3−OMe−6−ACNH−4−Py]、[5826:2−OMe−6−ACNH−4−Py]、[5827:5−OMe−6−ACNH−4−Py]、[5828:3−(N−AC−N−Me−N)−4−Py]、[5829:2−Cl−3−(N−AC−N−Me−N)−4−Py]、[5830:5−Cl−3−(N−AC−N−Me−N)−4−Py]、[5831:6−Cl−3−(N−AC−N−Me−N)−4−Py]、[5832:2−Me−3−(N−AC−N−Me−N)−4−Py]、[5833:5−Me−3−(N−AC−N−Me−N)−4−Py]、[5834:6−Me−3−(N−AC−N−Me−N)−4−Py]、[5835:2−CF3−3−(N−AC−N−Me−N)−4−Py]、[5836:5−CF3−3−(N−AC−N−Me−N)−4−Py]、[5837:6−CF3−3−(N−AC−N−Me−N)−4−Py]、[5838:2−CN−3−(N−AC−N−Me−N)−4−Py]、[5839:5−CN−3−(N−AC−N−Me−N)−4−Py]、[5840:6−CN−3−(N−AC−N−Me−N)−4−Py]、[5841:2−OMe−3−(N−AC−N−Me−N)−4−Py]、[5842:5−OMe−3−(N−AC−N−Me−N)−4−Py]、[5843:6−OMe−3−(N−AC−N−Me−N)−4−Py]、[5844:2−(N−AC−N−Me−N)−4−Py]、[5845:3−Cl−2−(N−AC−N−Me−N)−4−Py]、[5846:5−Cl−2−(N−AC−N−Me−N)−4−Py]、[5847:6−Cl−2−(N−AC−N−Me−N)−4−Py]、[5848:3−Me−2−(N−AC−N−Me−N)−4−Py]、[5849:5−Me−2−(N−AC−N−Me−N)−4−Py]、[5850:6−Me−2−(N−AC−N−Me−N)−4−Py]、[5851:3−CF3−2−(N−AC−N−Me−N)−4−Py]、[5852:5−CF3−2−(N−AC−N−Me−N)−4−Py]、[5853:6−CF3−2−(N−AC−N−Me−N)−4−Py]、[5854:3−CN−2−(N−AC−N−Me−N)−4−Py]、[5855:5−CN−2−(N−AC−N−Me−N)−4−Py]、[5856:6−CN−2−(N−AC−N−Me−N)−4−Py]、[5857:3−OMe−2−(N−AC−N−Me−N)−4−Py]、[5858:5−OMe−2−(N−AC−N−Me−N)−4−Py]、[5859:6−OMe−2−(N−AC−N−Me−N)−4−Py]、[5860:5−(N−AC−N−Me−N)−4−Py]、[5861:3−Cl−5−(N−AC−N−Me−N)−4−Py]、[5862:2−Cl−5−(N−AC−N−Me−N)−4−Py]、[5863:6−Cl−5−(N−AC−N−Me−N)−4−Py]、[5864:3−Me−5−(N−AC−N−Me−N)−4−Py]、[5865:2−Me−5−(N−AC−N−Me−N)−4−Py]、[5866:6−Me−5−(N−AC−N−Me−N)−4−Py]、[5867:3−CF3−5−(N−AC−N−Me−N)−4−Py]、[5868:2−CF3−5−(N−AC−N−Me−N)−4−Py]、[5869:6−CF3−5−(N−AC−N−Me−N)−4−Py]、[5870:3−CN−5−(N−AC−N−Me−N)−4−Py]、[5871:2−CN−5−(N−AC−N−Me−N)−4−Py]、[5872:6−CN−5−(N−AC−N−Me−N)−4−Py]、[5873:3−OMe−5−(N−AC−N−Me−N)−4−Py]、[5874:2−OMe−5−(N−AC−N−Me−N)−4−Py]、[5875:6−OMe−5−(N−AC−N−Me−N)−4−Py]、[5876:6−(N−AC−N−Me−N)−4−Py]、[5877:3−Cl−6−(N−AC−N−Me−N)−4−Py]、[5878:2−Cl−6−(N−AC−N−Me−N)−4−Py]、[5879:5−Cl−6−(N−AC−N−Me−N)−4−Py]、[5880:3−Me−6−(N−AC−N−Me−N)−4−Py]、[5881:2−Me−6−(N−AC−N−Me−N)−4−Py]、[5882:5−Me−6−(N−AC−N−Me−N)−4−Py]、[5883:3−CF3−6−(N−AC−N−Me−N)−4−Py]、[5884:2−CF3−6−(N−AC−N−Me−N)−4−Py]、[5885:5−CF3−6−(N−AC−N−Me−N)−4−Py]、[5886:3−CN−6−(N−AC−N−Me−N)−4−Py]、[5887:2−CN−6−(N−AC−N−Me−N)−4−Py]、[5888:5−CN−6−(N−AC−N−Me−N)−4−Py]、[5889:3−OMe−6−(N−AC−N−Me−N)−4−Py]、[5890:2−OMe−6−(N−AC−N−Me−N)−4−Py]、[5891:5−OMe−6−(N−AC−N−Me−N)−4−Py]、[5892:3−AC−4−Py]、[5893:2−Cl−3−AC−4−Py]、[5894:5−Cl−3−AC−4−Py]、[5895:6−Cl−3−AC−4−Py]、[5896:2−Me−3−AC−4−Py]、[5897:5−Me−3−AC−4−Py]、[5898:6−Me−3−AC−4−Py]、[5899:2−CF3−3−AC−4−Py]、[5900:5−CF3−3−AC−4−Py]、 [5801: 2-Me-5-ACNH-4-Py], [5802: 6-Me-5-ACNH-4-Py], [5803: 3-CF3-5-ACNH-4-Py], [5804 : 2-CF3-5-ACNH-4-Py], [5805: 6-CF3-5-ACNH-4-Py], [5806: 3-CN-5-ACNH-4-Py], [5807: 2 -CN-5-ACNH-4-Py], [5808: 6-CN-5-ACNH-4-Py], [5809: 3-OMe-5-ACNH-4-Py], [5810: 2-OMe -5-ACNH-4-Py], [5811: 6-OMe-5-ACNH-4-Py], [5812: 6-ACNH-4-Py], [5813: 3-Cl-6-ACNH-4 -Py], [5814: 2-Cl-6-ACNH-4- y], [5815: 5-Cl-6-ACNH-4-Py], [5816: 3-Me-6-ACNH-4-Py], [5817: 2-Me-6-ACNH-4-Py] [5818: 5-Me-6-ACNH-4-Py], [5819: 3-CF3-6-ACNH-4-Py], [5820: 2-CF3-6-ACNH-4-Py], [ 5821: 5-CF3-6-ACNH-4-Py], [5822: 3-CN-6-ACNH-4-Py], [5823: 2-CN-6-ACNH-4-Py], [5824: 5-CN-6-ACNH-4-Py], [5825: 3-OMe-6-ACNH-4-Py], [5826: 2-OMe-6-ACNH-4-Py], [5827: 5- OMe-6-ACNH-4-Py], [5828: 3- (N- CN-Me-N) -4-Py], [5829: 2-Cl-3- (N-AC-N-Me-N) -4-Py], [5830: 5-Cl-3- ( N-AC-N-Me-N) -4-Py], [5831: 6-Cl-3- (N-AC-N-Me-N) -4-Py], [5832: 2-Me-3. -(N-AC-N-Me-N) -4-Py], [5833: 5-Me-3- (N-AC-N-Me-N) -4-Py], [5834: 6-Me -3- (N-AC-N-Me-N) -4-Py], [5835: 2-CF3-3 (N-AC-N-Me-N) -4-Py], [5836: 5 -CF3-3- (N-AC-N-Me-N) -4-Py], [5837: 6-CF3-3- (N-AC-N-Me-N) -4-Py], [5838. : 2-CN-3- (NA CN-Me-N) -4-Py], [5839: 5-CN-3- (N-AC-N-Me-N) -4-Py], [5840: 6-CN-3- ( N-AC-N-Me-N) -4-Py], [5841: 2-OMe-3- (N-AC-N-Me-N) -4-Py], [5842: 5-OMe-3. -(N-AC-N-Me-N) -4-Py], [5843: 6-OMe-3- (N-AC-N-Me-N) -4-Py], [5844: 2- ( N-AC-N-Me-N) -4-Py], [5845: 3-Cl-2- (N-AC-N-Me-N) -4-Py], [5846: 5-Cl-2. -(N-AC-N-Me-N) -4-Py], [5847: 6-Cl-2- (N-AC-N-Me-N) -4-Py], [5848: 3-Me. -2- (N-AC-N-M -N) -4-Py], [5849: 5-Me-2- (N-AC-N-Me-N) -4-Py], [5850: 6-Me-2- (N-AC-N). -Me-N) -4-Py], [5851: 3-CF3-2- (N-AC-N-Me-N) -4-Py], [5852: 5-CF3-2- (N-AC). -N-Me-N) -4-Py], [5853: 6-CF3-2- (N-AC-N-Me-N) -4-Py], [5854: 3-CN-2- (N -AC-N-Me-N) -4-Py], [5855: 5-CN-2- (N-AC-N-Me-N) -4-Py], [5856: 6-CN-2- (N-AC-N-Me-N) -4-Py], [5857: 3-OMe-2- (N-AC-N-Me-N) -4-Py], [5858: 5-OMe- 2- (N-AC-N Me-N) -4-Py], [5859: 6-OMe-2- (N-AC-N-Me-N) -4-Py], [5860: 5- (N-AC-N-Me- N) -4-Py], [5861: 3-Cl-5- (N-AC-N-Me-N) -4-Py], [5862: 2-Cl-5- (N-AC-N- Me-N) -4-Py], [5863: 6-Cl-5- (N-AC-N-Me-N) -4-Py], [5864: 3-Me-5- (N-AC- N-Me-N) -4-Py], [5865: 2-Me-5- (N-AC-N-Me-N) -4-Py], [5866: 6-Me-5- (N- AC-N-Me-N) -4-Py], [5867: 3-CF3-5- (N-AC-N-Me-N) -4-Py], [5868: 2-CF3-5- ( N-AC-N-Me-N) -4-Py], [5869: 6-CF3-5- (N-AC-N-Me-N) -4-Py], [5870: 3-CN-5- (N-AC-N-Me- N) -4-Py], [5871: 2-CN-5- (N-AC-N-Me-N) -4-Py], [5872: 6-CN-5- (N-AC-N- Me-N) -4-Py], [5873: 3-OMe-5- (N-AC-N-Me-N) -4-Py], [5874: 2-OMe-5- (N-AC- N-Me-N) -4-Py], [5875: 6-OMe-5- (N-AC-N-Me-N) -4-Py], [5876: 6- (N-AC-N- Me-N) -4-Py], [5877: 3-Cl-6- (N-AC-N-Me-N) -4-Py], [5878: 2-Cl-6- (N-AC- N-Me-N) -4-P ], [5879: 5-Cl-6- (N-AC-N-Me-N) -4-Py], [5880: 3-Me-6- (N-AC-N-Me-N) -4. -Py], [5881: 2-Me-6- (N-AC-N-Me-N) -4-Py], [5882: 5-Me-6- (N-AC-N-Me-N) -4-Py], [5883: 3-CF3-6- (N-AC-N-Me-N) -4-Py], [5884: 2-CF3-6- (N-AC-N-Me- N) -4-Py], [5885: 5-CF3-6- (N-AC-N-Me-N) -4-Py], [5886: 3-CN-6- (N-AC-N- Me-N) -4-Py], [5887: 2-CN-6- (N-AC-N-Me-N) -4-Py], [5888: 5-CN-6- (N-AC- N-Me-N) -4-P ], [5889: 3-OMe-6- (N-AC-N-Me-N) -4-Py], [5890: 2-OMe-6- (N-AC-N-Me-N) -4. -Py], [5891: 5-OMe-6- (N-AC-N-Me-N) -4-Py], [5892: 3-AC-4-Py], [5893: 2-Cl-3. -AC-4-Py], [5894: 5-Cl-3-AC-4-Py], [5895: 6-Cl-3-AC-4-Py], [5896: 2-Me-3-AC. -4-Py], [5897: 5-Me-3-AC-4-Py], [5898: 6-Me-3-AC-4-Py], [5899: 2-CF3-3-AC-4. -Py], [5900: 5-CF3-3-3-AC-4-Py],
[5901:6−CF3−3−AC−4−Py]、[5902:2−CN−3−AC−4−Py]、[5903:5−CN−3−AC−4−Py]、[5904:6−CN−3−AC−4−Py]、[5905:2−OMe−3−AC−4−Py]、[5906:5−OMe−3−AC−4−Py]、[5907:6−OMe−3−AC−4−Py]、[5908:2−AC−4−Py]、[5909:3−Cl−2−AC−4−Py]、[5910:5−Cl−2−AC−4−Py]、[5911:6−Cl−2−AC−4−Py]、[5912:3−Me−2−AC−4−Py]、[5913:5−Me−2−AC−4−Py]、[5914:6−Me−2−AC−4−Py]、[5915:3−CF3−2−AC−4−Py]、[5916:5−CF3−2−AC−4−Py]、[5917:6−CF3−2−AC−4−Py]、[5918:3−CN−2−AC−4−Py]、[5919:5−CN−2−AC−4−Py]、[5920:6−CN−2−AC−4−Py]、[5921:3−OMe−2−AC−4−Py]、[5922:5−OMe−2−AC−4−Py]、[5923:6−OMe−2−AC−4−Py]、[5924:5−AC−4−Py]、[5925:3−Cl−5−AC−4−Py]、[5926:2−Cl−5−AC−4−Py]、[5927:6−Cl−5−AC−4−Py]、[5928:3−Me−5−AC−4−Py]、[5929:2−Me−5−AC−4−Py]、[5930:6−Me−5−AC−4−Py]、[5931:3−CF3−5−AC−4−Py]、[5932:2−CF3−5−AC−4−Py]、[5933:6−CF3−5−AC−4−Py]、[5934:3−CN−5−AC−4−Py]、[5935:2−CN−5−AC−4−Py]、[5936:6−CN−5−AC−4−Py]、[5937:3−OMe−5−AC−4−Py]、[5938:2−OMe−5−AC−4−Py]、[5939:6−OMe−5−AC−4−Py]、[5940:6−AC−4−Py]、[5941:3−Cl−6−AC−4−Py]、[5942:2−Cl−6−AC−4−Py]、[5943:5−Cl−6−AC−4−Py]、[5944:3−Me−6−AC−4−Py]、[5945:2−Me−6−AC−4−Py]、[5946:5−Me−6−AC−4−Py]、[5947:3−CF3−6−AC−4−Py]、[5948:2−CF3−6−AC−4−Py]、[5949:5−CF3−6−AC−4−Py]、[5950:3−CN−6−AC−4−Py]、[5951:2−CN−6−AC−4−Py]、[5952:5−CN−6−AC−4−Py]、[5953:3−OMe−6−AC−4−Py]、[5954:2−OMe−6−AC−4−Py]、[5955:5−OMe−6−AC−4−Py]、[5956:1,2−(メチレンジオキシ)フェニル−4−イル]、[5957:2,3−ジヒドロベンゾフラン−5−イル]、[5958:2,3−ジヒドロベンゾフラン−6−イル]、[5959:1,3−ジヒドロイソベンゾフラン−5−イル]、[5960:ベンゾフラン−5−イル]、[5961:ベンゾフラン−6−イル]、[5962:2,3−ジヒドロベンゾチオフェン−5−イル]、[5963:2,3−ジヒドロベンゾチオフェン−6−イル]、[5964:1,3−ジヒドロイソベンゾチオフェン−5−イル]、[5965:ベンゾチオフェン−5−イル]、[5966:ベンゾチオフェン−6−イル]、[5967:ベンゾジオキサン−4−イル]、[5968:クロマン−6−イル]、[5969:クロマン−7−イル]、[5970:イソクロマン−6−イル]、[5971:イソクロマン−7−イル]、[5972:フェニル]、[5973:2−フルオロフェニル]、[5974:3−フルオロフェニル]、[5975:4−フルオロフェニル]、[5976:2,4−ジフルオロフェニル]、[5977:2,4,6−トリフルオロフェニル]、[5978:2,3,4,5,6−ペンタフルオロフェニル]、[5979:2,3−ジフルオロフェニル]、[5980:2−クロロフェニル]、[5981:3−クロロフェニル]、[5982:4−クロロフェニル]、[5983:2,3−ジクロロフェニル]、[5984:2,4−ジクロロフェニル]、[5985:2,5−ジクロロフェニル]、[5986:2,6−ジクロロフェニル]、[5987:3,4−ジクロロフェニル]、[5988:3,5−ジクロロフェニル]、[5989:2,3,4−トリクロロフェニル]、[5990:2,3,5−トリクロロフェニル]、[5991:2,3,6−トリクロロフェニル]、[5992:2,4,5−トリクロロフェニル]、[5993:2,4,6−トリクロロフェニル]、[5994:3,4,5−トリクロロフェニル]、[5995:2,3,4,6−テトラクロロフェニル]、[5996:2,3,5,6−テトラクロロフェニル]、[5997:2,3,4,5,6−ペンタクロロフェニル]、[5998:2−ブロモフェニル]、[5999:3−ブロモフェニル]、[6000:4−ブロモフェニル]、 [5901: 6-CF3-3-3-AC-4-Py], [5902: 2-CN-3-AC-4-Py], [5903: 5-CN-3-AC-4-Py], [5904 : 6-CN-3-AC-4-Py], [5905: 2-OMe-3-AC-4-Py], [5906: 5-OMe-3-AC-4-Py], [5907: 6. -OMe-3-AC-4-Py], [5908: 2-AC-4-Py], [5909: 3-Cl-2-AC-4-Py], [5910: 5-Cl-2-AC -4-Py], [5911: 6-Cl-2-AC-4-Py], [5912: 3-Me-2-AC-4-Py], [5913: 5-Me-2-AC-4 -Py], [5914: 6-Me-2-AC-4-Py], [5915: 3-CF3-2-AC-4-Py], [59 6: 5-CF3-2-AC-4-Py], [5917: 6-CF3-2-AC-4-Py], [5918: 3-CN-2-AC-4-Py], [5919: 5-CN-2-AC-4-Py], [5920: 6-CN-2-AC-4-Py], [5921: 3-OMe-2-AC-4-Py], [5922: 5- OMe-2-AC-4-Py], [5923: 6-OMe-2-AC-4-Py], [5924: 5-AC-4-Py], [5925: 3-Cl-5-AC- 4-Py], [5926: 2-Cl-5-AC-4-Py], [5927: 6-Cl-5-AC-4-Py], [5928: 3-Me-5-AC-4- Py], [5929: 2-Me-5-AC-4-Py], [5930: 6-Me-5-AC-4-Py], [5931: -CF3-5-AC-4-Py], [5932: 2-CF3-5-AC-4-Py], [5933: 6-CF3-5-AC-4-Py], [5934: 3-CN. -5-AC-4-Py], [5935: 2-CN-5-AC-4-Py], [5936: 6-CN-5-AC-4-Py], [5937: 3-OMe-5. -AC-4-Py], [5938: 2-OMe-5-AC-4-Py], [5939: 6-OMe-5-AC-4-Py], [5940: 6-AC-4-Py]. ], [5941: 3-Cl-6-AC-4-Py], [5942: 2-Cl-6-AC-4-Py], [5943: 5-Cl-6-AC-4-Py], [5944: 3-Me-6-AC-4-Py], [5945: 2-Me-6-AC-4-Py], [5946: 5-M e-6-AC-4-Py], [5947: 3-CF3-6-AC-4-Py], [5948: 2-CF3-6-AC-4-Py], [5949: 5-CF3- 6-AC-4-Py], [5950: 3-CN-6-AC-4-Py], [5951: 2-CN-6-AC-4-Py], [5952: 5-CN-6 AC-4-Py], [5953: 3-OMe-6-AC-4-Py], [5954: 2-OMe-6-AC-4-Py], [5955: 5-OMe-6-AC- 4-Py], [5956: 1,2- (methylenedioxy) phenyl-4-yl], [5957: 2,3-dihydrobenzofuran-5-yl], [5958: 2,3-dihydrobenzofuran-6. -Yl], [5959: 1,3-dihydroisobenzofuran-5-yl], [5 60: benzofuran-5-yl], [5961: benzofuran-6-yl], [5962: 2,3-dihydrobenzothiophen-5-yl], [5963: 2,3-dihydrobenzothiophen-6-yl] [5964: 1,3-dihydroisobenzothiophen-5-yl], [5965: benzothiophen-5-yl], [5966: benzothiophen-6-yl], [5967: benzodioxan-4-yl]. [5968: Chroman-6-yl], [5969: Chroman-7-yl], [5970: Isochroman-6-yl], [5971: Isochroman-7-yl], [5972: Phenyl], [5973: 2-fluorophenyl], [5974: 3-fluorophenyl], [5975: 4-fluorophenyl], [5976: 2 4-difluorophenyl], [5977: 2,4,6-trifluorophenyl], [5978: 2,3,4,5,6-pentafluorophenyl], [5979: 2,3-difluorophenyl], [ 5980: 2-chlorophenyl], [5981: 3-chlorophenyl], [5982: 4-chlorophenyl], [5983: 2,3-dichlorophenyl], [5984: 2,4-dichlorophenyl], [5985: 2,5- Dichlorophenyl], [5986: 2,6-dichlorophenyl], [5987: 3,4-dichlorophenyl], [5988: 3,5-dichlorophenyl], [5989: 2,3,4-trichlorophenyl], [5990: 2 , 3,5-trichlorophenyl], [5991: 2,3,6-trichlorophenyl], [5992: 2,4,5-trichlorophenyl], [5993: 2,4,6-trichlorophenyl], [5994: 3,4,5-trichlorophenyl], [5995: 2,3,4,6-tetrachlorophenyl] [5996: 2,3,5,6-tetrachlorophenyl], [5997: 2,3,4,5,6-pentachlorophenyl], [5998: 2-bromophenyl], [5999: 3-bromophenyl]. [6000: 4-bromophenyl],
[6001:2,4−ジブロモフェニル]、[6002:2,5−ジブロモフェニル]、[6003:2,6−ジブロモフェニル]、[6004:2,4,6−トリブロモフェニル]、[6005:2,3,4,5,6−ペンタブロモフェニル]、[6006:2−ヨードフェニル]、[6007:3−ヨードフェニル]、[6008:4−ヨードフェニル]、[6009:2,4−ジヨードフェニル]、[6010:2−クロロ−3−フルオロフェニル]、[6011:2−クロロ−4−フルオロフェニル]、[6012:2−クロロ−5−フルオロフェニル]、[6013:2−クロロ−6−フルオロフェニル]、[6014:2−クロロ−3−ブロモフェニル]、[6015:2−クロロ−4−ブロモフェニル]、[6016:2−クロロ−5−ブロモフェニル]、[6017:2−クロロ−6−ブロモフェニル]、[6018:2−ブロモ−3−クロロフェニル]、[6019:2−ブロモ−4−クロロフェニル]、[6020:2−ブロモ−5−クロロフェニル]、[6021:2−ブロモ−3−フルオロフェニル]、[6022:2−ブロモ−4−フルオロフェニル]、[6023:2−ブロモ−5−フルオロフェニル]、[6024:2−ブロモ−6−フルオロフェニル]、[6025:2−フルオロ−3−クロロフェニル]、[6026:2−フルオロ−4−クロロフェニル]、[6027:2−フルオロ−5−クロロフェニル]、[6028:2−フルオロ−4−ブロモフェニル]、[6029:3−クロロ−4−フルオロフェニル]、[6030:3−クロロ−5−フルオロフェニル]、[6031:3−クロロ−4−ブロモフェニル]、[6032:3−クロロ−5−ブロモフェニル]、[6033:3−フルオロ−4−クロロフェニル]、[6034:3−フルオロ−4−ブロモフェニル]、[6035:3−ブロモ−4−クロロフェニル]、[6036:3−ブロモ−4−フルオロフェニル]、[6037:2,6−ジクロロ−4−ブロモフェニル]、[6038:2,3−ジフルオロ−4−クロロフェニル]、[6039:2,6−ジフルオロ−4−クロロフェニル]、[6040:2,5−ジフルオロ−4−クロロフェニル]、[6041:3,5−ジフルオロ−4−クロロフェニル]、[6042:2,3,5−トリフルオロ−4−クロロフェニル]、[6043:2,3,6−トリフルオロ−4−クロロフェニル]、[6044:2,3,5,6−テトラフルオロ−4−クロロフェニル]、[6045:2−フルオロ−4−ブロモフェニル]、[6046:2,3−ジフルオロ−4−ブロモフェニル]、[6047:2,6−ジフルオロ−4−ブロモフェニル]、[6048:2,5−ジフルオロ−4−ブロモフェニル]、[6049:3,5−ジフルオロ−4−ブロモフェニル]、[6050:2,3,5−トリフルオロ−4−ブロモフェニル]、[6051:2,3,6−トリフルオロ−4−ブロモフェニル]、[6052:2,3,5,6−テトラフルオロ−4−ブロモフェニル]、[6053:2−フルオロ−4−ヨードフェニル]、[6054:3−フルオロ−4−ヨードフェニル]、[6055:2,3−ジフルオロ−4−ヨードフェニル]、[6056:2,6−ジフルオロ−4−ヨードフェニル]、[6057:2,5−ジフルオロ−4−ヨードフェニル]、[6058:3,5−ジフルオロ−4−ヨードフェニル]、[6059:2,3,5−トリフルオロ−4−ヨードフェニル]、[6060:2,3,6−トリフルオロ−4−ヨードフェニル]、[6061:2,3,5,6−テトラフルオロ−4−ヨードフェニル]、[6062:2−メチルフェニル]、[6063:3−メチルフェニル]、[6064:4−メチルフェニル]、[6065:2,3−ジメチルフェニル]、[6066:2,4−ジメチルフェニル]、[6067:2,5−ジメチルフェニル]、[6068:2,6−ジメチルフェニル]、[6069:3,4−ジメチルフェニル]、[6070:3,5−ジメチルフェニル]、[6071:2,3,5−トリメチルフェニル]、[6072:2,3,4−トリメチルフェニル]、[6073:2,3,6−トリメチルフェニル]、[6074:2,4,5−トリメチルフェニル]、[6075:2,4,6−トリメチルフェニル]、[6076:3,4,5−トリメチルフェニル]、[6077:2,3,4,6−テトラメチルフェニル]、[6078:2,3,5,6−テトラメチルフェニル]、[6079:2,3,4,5,6−ペンタメチルフェニル]、[6080:2−エチルフェニル]、[6081:3−エチルフェニル]、[6082:4−エチルフェニル]、[6083:2,4−ジエチルフェニル]、[6084:2,6−ジエチルフェニル]、[6085:3,5−ジエチルフェニル]、[6086:2,4,6−トリエチルフェニル]、[6087:2−n−プロピルフェニル]、[6088:3−n−プロピルフェニル]、[6089:4−n−プロピルフェニル]、[6090:2−イソプロピルフェニル]、[6091:3−イソプロピルフェニル]、[6092:4−イソプロピルフェニル]、[6093:2,4−ジイソプロピルフェニル]、[6094:2,6−ジイソプロピルフェニル]、[6095:3,5−ジイソプロピルフェニル]、[6096:2−s−ブチルフェニル]、[6097:3−s−ブチルフェニル]、[6098:4−s−ブチルフェニル]、[6099:2−t−ブチルフェニル]、[6100:3−t−ブチルフェニル]、 [6001: 2,4-dibromophenyl], [6002: 2,5-dibromophenyl], [6003: 2,6-dibromophenyl], [6004: 2,4,6-tribromophenyl], [6005: 2,3,4,5,6-pentabromophenyl], [6006: 2-iodophenyl], [6007: 3-iodophenyl], [6008: 4-iodophenyl], [6009: 2,4-di Iodophenyl], [6010: 2-chloro-3-fluorophenyl], [6011: 2-chloro-4-fluorophenyl], [6012: 2-chloro-5-fluorophenyl], [6013: 2-chloro- 6-fluorophenyl], [6014: 2-chloro-3-bromophenyl], [6015: 2-chloro-4-bromophenyl], [6016: 2- Ro-5-bromophenyl], [6017: 2-chloro-6-bromophenyl], [6018: 2-bromo-3-chlorophenyl], [6019: 2-bromo-4-chlorophenyl], [6020: 2- Bromo-5-chlorophenyl], [6021: 2-bromo-3-fluorophenyl], [6022: 2-bromo-4-fluorophenyl], [6023: 2-bromo-5-fluorophenyl], [6024: 2 -Bromo-6-fluorophenyl], [6025: 2-fluoro-3-chlorophenyl], [6026: 2-fluoro-4-chlorophenyl], [6027: 2-fluoro-5-chlorophenyl], [6028: 2- Fluoro-4-bromophenyl], [6029: 3-chloro-4-fluorophenyl], [6030: 3-chloro 5-fluorophenyl], [6031: 3-chloro-4-bromophenyl], [6032: 3-chloro-5-bromophenyl], [6033: 3-fluoro-4-chlorophenyl], [6034: 3-fluoro -4-bromophenyl], [6035: 3-bromo-4-chlorophenyl], [6036: 3-bromo-4-fluorophenyl], [6037: 2,6-dichloro-4-bromophenyl], [6038: 2,3-difluoro-4-chlorophenyl], [6039: 2,6-difluoro-4-chlorophenyl], [6040: 2,5-difluoro-4-chlorophenyl], [6041: 3,5-difluoro-4- Chlorophenyl], [6042: 2,3,5-trifluoro-4-chlorophenyl], [6043: 2,3,6-trifluoro Oro-4-chlorophenyl], [6044: 2,3,5,6-tetrafluoro-4-chlorophenyl], [6045: 2-fluoro-4-bromophenyl], [6046: 2,3-difluoro-4- Bromophenyl], [6047: 2,6-difluoro-4-bromophenyl], [6048: 2,5-difluoro-4-bromophenyl], [6049: 3,5-difluoro-4-bromophenyl], [ 6050: 2,3,5-trifluoro-4-bromophenyl], [6051: 2,3,6-trifluoro-4-bromophenyl], [6052: 2,3,5,6-tetrafluoro-4 -Bromophenyl], [6053: 2-fluoro-4-iodophenyl], [6054: 3-fluoro-4-iodophenyl], [6055: 2,3-diflu] Rho-4-iodophenyl], [6056: 2,6-difluoro-4-iodophenyl], [6057: 2,5-difluoro-4-iodophenyl], [6058: 3,5-difluoro-4-iodo Phenyl], [6059: 2,3,5-trifluoro-4-iodophenyl], [6060: 2,3,6-trifluoro-4-iodophenyl], [6061: 2,3,5,6- Tetrafluoro-4-iodophenyl], [6062: 2-methylphenyl], [6063: 3-methylphenyl], [6064: 4-methylphenyl], [6065: 2,3-dimethylphenyl], [6066: 2,4-dimethylphenyl], [6067: 2,5-dimethylphenyl], [6068: 2,6-dimethylphenyl], [6069: 3,4-dimethyl Enyl], [6070: 3,5-dimethylphenyl], [6071: 2,3,5-trimethylphenyl], [6072: 2,3,4-trimethylphenyl], [6073: 2,3,6-trimethyl] Phenyl], [6074: 2,4,5-trimethylphenyl], [6075: 2,4,6-trimethylphenyl], [6076: 3,4,5-trimethylphenyl], [6077: 2,3,4 , 6-tetramethylphenyl], [6078: 2,3,5,6-tetramethylphenyl], [6079: 2,3,4,5,6-pentamethylphenyl], [6080: 2-ethylphenyl] [6081: 3-ethylphenyl], [6082: 4-ethylphenyl], [6083: 2,4-diethylphenyl], [6084: 2,6-diethylphenyl] [6085: 3,5-diethylphenyl], [6086: 2,4,6-triethylphenyl], [6087: 2-n-propylphenyl], [6088: 3-n-propylphenyl], [6089: 4-n-propylphenyl], [6090: 2-isopropylphenyl], [6091: 3-isopropylphenyl], [6092: 4-isopropylphenyl], [6093: 2,4-diisopropylphenyl], [6094: 2 , 6-diisopropylphenyl], [6095: 3,5-diisopropylphenyl], [6096: 2-s-butylphenyl], [6097: 3-s-butylphenyl], [6098: 4-s-butylphenyl]. [6099: 2-t-butylphenyl], [6100: 3-t-butylphenyl],
[6101:4−t−ブチルフェニル]、[6102:4−n−ブチルフェニル]、[6103:4−n−ノニルフェニル]、[6104:2−メチル−4−t−ブチルフェニル]、[6105:2−メチル−6−t−ブチルフェニル]、[6106:2−メチル−4−イソプロピルフェニル]、[6107:2−メチル−5−イソプロピルフェニル]、[6108:3−メチル−4−イソプロピルフェニル]、[6109:2−シクロヘキシルフェニル]、[6110:3−シクロヘキシルフェニル]、[6111:4−シクロヘキシルフェニル]、[6112:4−シクロプロピルフェニル]、[6113:4−シクロブチルフェニル]、[6114:4−シクロペンチルフェニル]、[6115:2−クロロ−4−フェニルフェニル]、[6116:2−ブロモ−4−フェニルフェニル]、[6117:4−ヒドロキシフェニル]、[6118:2−メトキシフェニル]、[6119:3−メトキシフェニル]、[6120:4−メトキシフェニル]、[6121:2−エトキシフェニル]、[6122:3−エトキシフェニル]、[6123:4−エトキシフェニル]、[6124:2−n−プロピルオキシフェニル]、[6125:3−n−プロピルオキシフェニル]、[6126:4−n−プロピルオキシフェニル]、[6127:2−イソプロピルオキシフェニル]、[6128:3−イソプロピルオキシフェニル]、[6129:4−イソプロピルオキシフェニル]、[6130:2−n−ヘキシルオキシフェニル]、[6131:3−n−ヘキシルオキシフェニル]、[6132:4−n−ヘキシルオキシフェニル]、[6133:2−ベンジルオキシフェニル]、[6134:3−ベンジルオキシフェニル]、[6135:4−ベンジルオキシフェニル]、[6136:2,3−ジメトキシフェニル]、[6137:2,4−ジメトキシフェニル]、[6138:2,5−ジメトキシフェニル]、[6139:2,6−ジメトキシフェニル]、[6140:3,4−ジメトキシフェニル]、[6141:3,5−ジメトキシフェニル]、[6142:2−t−ブトキシフェニル]、[6143:3−t−ブトキシフェニル]、[6144:4−t−ブトキシフェニル]、[6145:3−(3’−クロロフェニル)フェニル]、[6146:4−(4’−クロルフェニル)フェニル]、[6147:2−フェノキシフェニル]、[6148:3−フェノキシフェニル]、[6149:4−フェノキシフェニル]、[6150:2−(2’−フルオロフェノキシ)フェニル]、[6151:3−(3’−クロロフェノキシ)フェニル]、[6152:4−(4’−クロルフェノキシ)フェニル]、[6153:2,3,6−トリメチル−4−フルオロフェニル]、[6154:2,3,6−トリメチル−4−クロロフェニル]、[6155:2,3,6−トリメチル−4−ブロモフェニル]、[6156:2,4−ジメチル−6−フルオロフェニル]、[6157:2,4−ジメチル−6−クロロフェニル]、[6158:2,4−ジメチル−6−ブロモフェニル]、[6159:2−イソプロピル−4−クロロ−5−メチルフェニル]、[6160:2−クロロ−4−ニトロフェニル]、[6161:2−ニトロ−4−クロロフェニル]、[6162:2−メトキシ−5−ニトロフェニル]、[6163:2,4−ジクロロ−5−ニトロフェニル]、[6164:2,4−ジクロロ−6−ニトロフェニル]、[6165:2,6−ジクロロ−4−ニトロフェニル]、[6166:2,6−ジブロモ−4−ニトロフェニル]、[6167:2,6−ジヨード−4−ニトロフェニル]、[6168:2−メチル−5−イソプロピル−4−クロロフェニル]、[6169:2−メトキシカルボニルフェニル]、[6170:3−メトキシカルボニルフェニル]、[6171:4−メトキシカルボニルフェニル]、[6172:4−アセトキシフェニル]、[6173:2−メトキシメチルフェニル]、[6174:3−メトキシメチルフェニル]、[6175:4−メトキシメチルフェニル]、[6176:2−フェニルフェニル]、[6177:3−フェニルフェニル]、[6178:4−フェニルフェニル]、[6179:2−(2’−フルオロフェニル)フェニル]、[6180:2−メチル−5−ブロモフェニル]、[6181:2−メチル−6−ブロモフェニル]、[6182:2−クロロ−3−メチルフェニル]、[6183:2−クロロ−4−メチルフェニル]、[6184:2−クロロ−5−メチルフェニル]、[6185:2−フルオロ−3−メチルフェニル]、[6186:2−フルオロ−4−メチルフェニル]、[6187:2−フルオロ−5−メチルフェニル]、[6188:2−ブロモ−3−メチルフェニル]、[6189:2−ブロモ−4−メチルフェニル]、[6190:2−ブロモ−5−メチルフェニル]、[6191:3−メチル−4−クロロフェニル]、[6192:3−メチル−5−クロロフェニル]、[6193:3−メチル−4−フルオロフェニル]、[6194:3−メチル−5−フルオロフェニル]、[6195:3−メチル−4−ブロモフェニル]、[6196:3−メチル−5−ブロモフェニル]、[6197:3−フルオロ−4−メチルフェニル]、[6198:3−クロロ−4−メチルフェニル]、[6199:3−ブロモ−4−メチルフェニル]、[6200:2−クロロ−4,5−ジメチルフェニル]、 [6101: 4-t-butylphenyl], [6102: 4-n-butylphenyl], [6103: 4-n-nonylphenyl], [6104: 2-methyl-4-t-butylphenyl], [6105 : 2-methyl-6-t-butylphenyl], [6106: 2-methyl-4-isopropylphenyl], [6107: 2-methyl-5-isopropylphenyl], [6108: 3-methyl-4-isopropylphenyl] ], [6109: 2-cyclohexylphenyl], [6111: 3-cyclohexylphenyl], [6111: 4-cyclohexylphenyl], [6112: 4-cyclopropylphenyl], [6113: 4-cyclobutylphenyl], [ 6114: 4-cyclopentylphenyl], [6115: 2-chloro-4-phenylphenyl] [6116: 2-Bromo-4-phenylphenyl], [6117: 4-hydroxyphenyl], [6118: 2-methoxyphenyl], [6119: 3-methoxyphenyl], [6120: 4-methoxyphenyl], [ 6121: 2-ethoxyphenyl], [6122: 3-ethoxyphenyl], [6123: 4-ethoxyphenyl], [6124: 2-n-propyloxyphenyl], [6125: 3-n-propyloxyphenyl], [6126: 4-n-propyloxyphenyl], [6127: 2-isopropyloxyphenyl], [6128: 3-isopropyloxyphenyl], [6129: 4-isopropyloxyphenyl], [6130: 2-n-hexyl Oxyphenyl], [6131: 3-n-hexyloxypheny ], [6132: 4-n-hexyloxyphenyl], [6133: 2-benzyloxyphenyl], [6134: 3-benzyloxyphenyl], [6135: 4-benzyloxyphenyl], [6136: 2, 3 -Dimethoxyphenyl], [6137: 2,4-dimethoxyphenyl], [6138: 2,5-dimethoxyphenyl], [6139: 2,6-dimethoxyphenyl], [6140: 3,4-dimethoxyphenyl], [ 6141: 3,5-dimethoxyphenyl], [6142: 2-t-butoxyphenyl], [6143: 3-t-butoxyphenyl], [6144: 4-t-butoxyphenyl], [6145: 3- (3 '-Chlorophenyl) phenyl], [6146: 4- (4'-chlorophenyl) phenyl], [6147: 2 -Phenoxyphenyl], [6148: 3-phenoxyphenyl], [6149: 4-phenoxyphenyl], [6150: 2- (2′-fluorophenoxy) phenyl], [6151: 3- (3′-chlorophenoxy) Phenyl], [6152: 4- (4′-chlorophenoxy) phenyl], [6153: 2,3,6-trimethyl-4-fluorophenyl], [6154: 2,3,6-trimethyl-4-chlorophenyl] [6155: 2,3,6-trimethyl-4-bromophenyl], [6156: 2,4-dimethyl-6-fluorophenyl], [6157: 2,4-dimethyl-6-chlorophenyl], [6158: 2,4-dimethyl-6-bromophenyl], [6159: 2-isopropyl-4-chloro-5-methylphenyl], [6 60: 2-chloro-4-nitrophenyl], [6161: 2-nitro-4-chlorophenyl], [6162: 2-methoxy-5-nitrophenyl], [6163: 2,4-dichloro-5-nitrophenyl] ], [6164: 2,4-dichloro-6-nitrophenyl], [6165: 2,6-dichloro-4-nitrophenyl], [6166: 2,6-dibromo-4-nitrophenyl], [6167: 2,6-diiodo-4-nitrophenyl], [6168: 2-methyl-5-isopropyl-4-chlorophenyl], [6169: 2-methoxycarbonylphenyl], [6170: 3-methoxycarbonylphenyl], [6171 : 4-methoxycarbonylphenyl], [6172: 4-acetoxyphenyl], [6173: 2-methoxymethyl. Enyl], [6174: 3-methoxymethylphenyl], [6175: 4-methoxymethylphenyl], [6176: 2-phenylphenyl], [6177: 3-phenylphenyl], [6178: 4-phenylphenyl], [6179: 2- (2′-fluorophenyl) phenyl], [6180: 2-methyl-5-bromophenyl], [6181: 2-methyl-6-bromophenyl], [6182: 2-chloro-3- Methylphenyl], [6183: 2-chloro-4-methylphenyl], [6184: 2-chloro-5-methylphenyl], [6185: 2-fluoro-3-methylphenyl], [6186: 2-fluoro- 4-methylphenyl], [6187: 2-fluoro-5-methylphenyl], [6188: 2-bromo-3-methylphenyl] Enyl], [6189: 2-bromo-4-methylphenyl], [6190: 2-bromo-5-methylphenyl], [6191: 3-methyl-4-chlorophenyl], [6192: 3-methyl-5- Chlorophenyl], [6193: 3-methyl-4-fluorophenyl], [6194: 3-methyl-5-fluorophenyl], [6195: 3-methyl-4-bromophenyl], [6196: 3-methyl-5 -Bromophenyl], [6197: 3-fluoro-4-methylphenyl], [6198: 3-chloro-4-methylphenyl], [6199: 3-bromo-4-methylphenyl], [6200: 2-chloro. -4,5-dimethylphenyl],
[6201:2−ブロモ−4,5−ジメチルフェニル]、[6202:2−クロロ−3,5−ジメチルフェニル]、[6203:2−ブロモ−3,5−ジメチルフェニル]、[6204:2,6−ジブロモ−4−メチルフェニル]、[6205:2,4−ジクロロ−6−メチルフェニル]、[6206:2,4−ジフルオロ−6−メチルフェニル]、[6207:2,4−ジブロモ−6−メチルフェニル]、[6208:2,6−ジメチル−4−フルオロフェニル]、[6209:2,6−ジメチル−4−クロロフェニル]、[6210:2,6−ジメチル−4−ブロモフェニル]、[6211:3,5−ジメチル−4−フルオロフェニル]、[6212:3,5−ジメチル−4−クロロフェニル]、[6213:3,5−ジメチル−4−ブロモフェニル]、[6214:2,3−ジフルオロ−4−メチルフェニル]、[6215:2,5−ジフルオロ−4−メチルフェニル]、[6216:3,5−ジフルオロ−4−メチルフェニル]、[6217:2,3,5−トリフルオロ−4−メチルフェニル]、[6218:2,3,6−トリフルオロ−4−メチルフェニル]、[6219:2,3,5,6−テトラフルオロ−4−メチルフェニル]、[6220:2−フルオロ−4−エチルフェニル]、[6221:3−フルオロ−4−エチルフェニル]、[6222:2,3−ジフルオロ−4−エチルフェニル]、[6223:2,6−ジフルオロ−4−エチルフェニル]、[6224:2,5−ジフルオロ−4−エチルフェニル]、[6225:3,5−ジフルオロ−4−エチルフェニル]、[6226:2,3,5−トリフルオロ−4−エチルフェニル]、[6227:2,3,6−トリフルオロ−4−エチルフェニル]、[6228:2,3,5,6−テトラフルオロ−4−エチルフェニル]、[6229:2−トリフルオロメチルフェニル]、[6230:3−トリフルオロメチルフェニル]、[6231:4−トリフルオロメチルフェニル]、[6232:4−(2,2,2−トリフルオロ−1−トリフルオロメチル−エチル)フェニル]、[6233:2−トリフルオロメトキシフェニル]、[6234:3−トリフルオロメトキシフェニル]、[6235:4−トリフルオロメトキシフェニル]、[6236:4−(2,2−ジフルオロエトキシ)フェニル]、[6237:4−(2,2,2−トリフルオロエトキシ)フェニル]、[6238:2−ニトロフェニル]、[6239:3−ニトロフェニル]、[6240:4−ニトロフェニル]、[6241:2−シアノフェニル]、[6242:3−シアノフェニル]、[6243:4−シアノフェニル]、[6244:2−メチル−3−クロロフェニル]、[6245:2−メチル−4−クロロフェニル]、[6246:2−メチル−5−クロロフェニル]、[6247:2−メチル−6−クロロフェニル]、[6248:2−メチル−3−フルオロフェニル]、[6249:2−メチル−4−フルオロフェニル]、[6250:2−メチル−5−フルオロフェニル]、[6251:2−メチル−6−フルオロフェニル]、[6252:2−メチル−3−ブロモフェニル]、[6253:2−メチル−4−ブロモフェニル]、[6254:4−メチルチオフェニル]、[6255:4−メチルスルホニルフェニル]、[6256:4−メチルスルフィニルフェニル]、[6257:4−トリフルオロメチルチオフェニル]、[6258:4−エチニルフェニル]、[6259:4−(1−プロピニル)フェニル]、[6260:4−ビニルフェニル]、[6261:4−(2,2−ジクロロビニル)フェニル]、[6262:4−(2,2−ジフルオロビニル)フェニル]、[6263:シクロヘキシル]、[6264:2−クロロシクロヘキシル]、[6265:3−クロロシクロヘキシル]、[6266:4−クロロシクロヘキシル]、[6267:4,4−ジクロロシクロヘキシル]、[6268:2−ブロモシクロヘキシル]、[6269:3−ブロモシクロヘキシル]、[6270:4−ブロモシクロヘキシル]、[6271:4,4−ジブロモシクロヘキシル]、[6272:2−ヨードシクロヘキシル]、[6273:3−ヨードシクロヘキシル]、[6274:4−ヨードシクロヘキシル]、[6275:2−フルオロシクロヘキシル ]、[6276:3−フルオロシクロヘキシル]、[6277:4−フルオロシクロヘキシル]、[6278:4,4−ジフルオロシクロヘキシル]、[6279:4−メチルシクロヘキシル]、[6280:4−エチルシクロヘキシル]、[6281:1−シクロヘキセニル]、[6282:2−シクロヘキセニル]、[6283:3−シクロヘキセニル]、[6284:2−クロロ−1−シクロヘキセニル]、[6285:3−クロロ−1−シクロヘキセニル]、[6286:4−クロロ−1−シクロヘキセニル]、[6287:5−クロロ−1−シクロヘキセニル]、[6288:6−クロロ−1−シクロヘキセニル]、[6289:1−クロロ−2−シクロヘキセニル]、[6290:2−クロロ−2−シクロヘキセニル]、[6291:3−クロロ−2−シクロヘキセニル]、[6292:4−クロロ−2−シクロヘキセニル]、[6293:5−クロロ−2−シクロヘキセニル]、[6294:6−クロロ−2−シクロヘキセニル]、[6295:1−クロロ−3−シクロヘキセニル]、[6296:2−クロロ−3−シクロヘキセニル]、[6297:3−クロロ−3−シクロヘキセニル]、[6298:4−クロロ−3−シクロヘキセニル]、[6299:5−クロロ−3−シクロヘキセニル]、[6300:6−クロロ−3−シクロヘキセニル]、 [6201: 2-bromo-4,5-dimethylphenyl], [6202: 2-chloro-3,5-dimethylphenyl], [6203: 2-bromo-3,5-dimethylphenyl], [6204: 2, 6-dibromo-4-methylphenyl], [6205: 2,4-dichloro-6-methylphenyl], [6206: 2,4-difluoro-6-methylphenyl], [6207: 2,4-dibromo-6 -Methylphenyl], [6208: 2,6-dimethyl-4-fluorophenyl], [6209: 2,6-dimethyl-4-chlorophenyl], [6210: 2,6-dimethyl-4-bromophenyl], [ 6211: 3,5-dimethyl-4-fluorophenyl], [6212: 3,5-dimethyl-4-chlorophenyl], [6213: 3,5-dimethyl-4-butyl Mophenyl], [6214: 2,3-difluoro-4-methylphenyl], [6215: 2,5-difluoro-4-methylphenyl], [6216: 3,5-difluoro-4-methylphenyl], [6217 : 2,3,5-trifluoro-4-methylphenyl], [6218: 2,3,6-trifluoro-4-methylphenyl], [6219: 2,3,5,6-tetrafluoro-4- Methylphenyl], [6220: 2-fluoro-4-ethylphenyl], [6221: 3-fluoro-4-ethylphenyl], [6222: 2,3-difluoro-4-ethylphenyl], [6223: 2, 6-difluoro-4-ethylphenyl], [6224: 2,5-difluoro-4-ethylphenyl], [6225: 3,5-difluoro-4-ethylphenyl] Nil], [6226: 2,3,5-trifluoro-4-ethylphenyl], [6227: 2,3,6-trifluoro-4-ethylphenyl], [6228: 2,3,5,6- Tetrafluoro-4-ethylphenyl], [6229: 2-trifluoromethylphenyl], [6230: 3-trifluoromethylphenyl], [6231: 4-trifluoromethylphenyl], [6232: 4- (2, 2,2-trifluoro-1-trifluoromethyl-ethyl) phenyl], [6233: 2-trifluoromethoxyphenyl], [6234: 3-trifluoromethoxyphenyl], [6235: 4-trifluoromethoxyphenyl] [6236: 4- (2,2-difluoroethoxy) phenyl], [6237: 4- (2,2,2-trifluoroe Toxi) phenyl], [6238: 2-nitrophenyl], [6239: 3-nitrophenyl], [6240: 4-nitrophenyl], [6241: 2-cyanophenyl], [6242: 3-cyanophenyl], [6243: 4-cyanophenyl], [6244: 2-methyl-3-chlorophenyl], [6245: 2-methyl-4-chlorophenyl], [6246: 2-methyl-5-chlorophenyl], [6247: 2- Methyl-6-chlorophenyl], [6248: 2-methyl-3-fluorophenyl], [6249: 2-methyl-4-fluorophenyl], [6250: 2-methyl-5-fluorophenyl], [6251: 2 -Methyl-6-fluorophenyl], [6252: 2-methyl-3-bromophenyl], [6253: 2-methyl. -4-bromophenyl], [6254: 4-methylthiophenyl], [6255: 4-methylsulfonylphenyl], [6256: 4-methylsulfinylphenyl], [6257: 4-trifluoromethylthiophenyl], [6258: 4-ethynylphenyl], [6259: 4- (1-propynyl) phenyl], [6260: 4-vinylphenyl], [6261: 4- (2,2-dichlorovinyl) phenyl], [6262: 4- ( 2,2-difluorovinyl) phenyl], [6263: cyclohexyl], [6264: 2-chlorocyclohexyl], [6265: 3-chlorocyclohexyl], [6266: 4-chlorocyclohexyl], [6267: 4,4- Dichlorocyclohexyl], [6268: 2-bromocyclohexyl], 6269: 3-bromocyclohexyl], [6270: 4-bromocyclohexyl], [6271: 4,4-dibromocyclohexyl], [6272: 2-iodocyclohexyl], [6273: 3-iodocyclohexyl], [6274: 4. -Iodocyclohexyl], [6275: 2-fluorocyclohexyl], [6276: 3-fluorocyclohexyl], [6277: 4-fluorocyclohexyl], [6278: 4,4-difluorocyclohexyl], [6279: 4-methylcyclohexyl. ], [6280: 4-ethylcyclohexyl], [6281: 1-cyclohexenyl], [6282: 2-cyclohexenyl], [6283: 3-cyclohexenyl], [6284: 2-chloro-1-cyclohexenyl]. , [628 : 3-chloro-1-cyclohexenyl], [6286: 4-chloro-1-cyclohexenyl], [6287: 5-chloro-1-cyclohexenyl], [6288: 6-chloro-1-cyclohexenyl], [6289: 1-chloro-2-cyclohexenyl], [6290: 2-chloro-2-cyclohexenyl], [6291: 3-chloro-2-cyclohexenyl], [6292: 4-chloro-2-cyclohexenyl] ], [6293: 5-chloro-2-cyclohexenyl], [6294: 6-chloro-2-cyclohexenyl], [6295: 1-chloro-3-cyclohexenyl], [6296: 2-chloro-3- Cyclohexenyl], [6297: 3-chloro-3-cyclohexenyl], [6298: 4-chloro-3-cyclohexenyl], [6 299: 5-chloro-3-cyclohexenyl], [6300: 6-chloro-3-cyclohexenyl],
[6301:4−ブロモ−1−シクロヘキセニル]、[6302:4−ブロモ−2−シクロヘキセニル]、[6303:4−ブロモ−3−シクロヘキセニル]、[6304:4−メチル−1−シクロヘキセニル]、[6305:4−メチル−2−シクロヘキセニル]、[6306:4−メチル−3−シクロヘキセニル]、[6307:4−エチル−1−シクロヘキセニル]、[6308:4−エチル−2−シクロヘキセニル]、[6309:4−エチル−3−シクロヘキセニル]、[6310:トリフルオロメチル ]、[6311:tert−ブチル]、[6312:3−フルオロ−2−メトキシフェニル]、[6313:4−フルオロ−2−メトキシフェニル]、[6314:5−フルオロ−2−メトキシフェニル]、[6315:6−フルオロ−2−メトキシフェニル]、[6316:3−クロロ−2−メトキシフェニル]、[6317:4−クロロ−2−メトキシフェニル]、[6318:5−クロロ−2−メトキシフェニル]、[6319:6−クロロ−2−メトキシフェニル]、[6320:3−ブロモ−2−メトキシフェニル]、[6321:4−ブロモ−2−メトキシフェニル]、[6322:5−ブロモ−2−メトキシフェニル]、[6323:6−ブロモ−2−メトキシフェニル]、[6324:3−ヨード−2−メトキシフェニル]、[6325:4−ヨード−2−メトキシフェニル]、[6326:5−ヨード−2−メトキシフェニル]、[6327:6−ヨード−2−メトキシフェニル]、[6328:2,3−ジメトキシフェニル]、[6329:2,4−ジメトキシフェニル]、[6330:2,5−ジメトキシフェニル]、[6331:2,6−ジメトキシフェニル]、[6332:3−メチル−2−メトキシフェニル]、[6333:4−メチル−2−メトキシフェニル]、[6334:5−メチル−2−メトキシフェニル]、[6335:6−メチル−2−メトキシフェニル]、[6336:3−エチル−2−メトキシフェニル]、[6337:4−エチル−2−メトキシフェニル]、[6338:5−エチル−2−メトキシフェニル]、[6339:6−エチル−2−メトキシフェニル]、[6340:3−トリフルオロメトキシ−2−メトキシフェニル]、[6341:4−トリフルオロメトキシ−2−メトキシフェニル]、[6342:5−トリフルオロメトキシ−2−メトキシフェニル]、[6343:6−トリフルオロメトキシ−2−メトキシフェニル]、[6344:3−トリフルオロメチル−2−メトキシフェニル]、[6345:4−トリフルオロメチル−2−メトキシフェニル]、[6346:5−トリフルオロメチル−2−メトキシフェニル]、[6347:6−トリフルオロメチル−2−メトキシフェニル]、[6348:3−メチルチオ−2−メトキシフェニル]、[6349:4−メチルチオ−2−メトキシフェニル]、[6350:5−メチルチオ−2−メトキシフェニル]、[6351:6−メチルチオ−2−メトキシフェニル]、[6352:3−トリフルオロメチルチオ−2−メトキシフェニル]、[6353:4−トリフルオロメチルチオ−2−メトキシフェニル]、[6354:5−トリフルオロメチルチオ−2−メトキシフェニル]、[6355:6−トリフルオロメチルチオ−2−メトキシフェニル]、[6356:3−エチニル−2−メトキシフェニル]、[6357:4−エチニル−2−メトキシフェニル]、[6358:5−エチニル−2−メトキシフェニル]、[6359:6−エチニル−2−メトキシフェニル]、[6360:3−シクロプロピル−2−メトキシフェニル]、[6361:4−シクロプロピル−2−メトキシフェニル]、[6362:5−シクロプロピル−2−メトキシフェニル]、[6363:6−シクロプロピル−2−メトキシフェニル]、[6364:3−シクロプロピルオキシ−2−メトキシフェニル]、[6365:4−シクロプロピルオキシ−2−メトキシフェニル]、[6366:5−シクロプロピルオキシ−2−メトキシフェニル]、[6367:6−シクロプロピルオキシ−2−メトキシフェニル]、[6368:2−エトキシ−3−フルオロフェニル]、[6369:2−エトキシ−4−フルオロフェニル]、[6370:2−エトキシ−5−フルオロフェニル]、[6371:2−エトキシ−6−フルオロフェニル]、[6372:3−クロロ−2−エトキシフェニル]、[6373:4−クロロ−2−エトキシフェニル]、[6374:5−クロロ−2−エトキシフェニル]、[6375:6−クロロ−2−エトキシフェニル]、[6376:3−ブロモ−2−エトキシフェニル]、[6377:4−ブロモ−2−エトキシフェニル]、[6378:5−ブロモ−2−エトキシフェニル]、[6379:6−ブロモ−2−エトキシフェニル]、[6380:2−エトキシ−3−ヨードフェニル]、[6381:2−エトキシ−4−ヨードフェニル]、[6382:2−エトキシ−5−ヨードフェニル]、[6383:2−エトキシ−6−ヨードフェニル]、[6384:2,3−ジエトキシフェニル]、[6385:2,4−ジエトキシフェニル]、[6386:2,5−ジエトキシフェニル]、[6387:2,6−ジエトキシフェニル]、[6388:2−エトキシ−3−メチルフェニル]、[6389:2−エトキシ−4−メチルフェニル]、[6390:2−エトキシ−5−メチルフェニル]、[6391:2−エトキシ−6−メチルフェニル]、[6392:3−エチル−2−エトキシフェニル]、[6393:4−エチル−2−エトキシフェニル]、[6394:5−エチル−2−エトキシフェニル]、[6395:6−エチル−2−エトキシフェニル]、[6396:2−エトキシ−3−トリフルオロメトキシフェニル]、[6397:2−エトキシ−4−トリフルオロメトキシフェニル]、[6398:2−エトキシ−5−トリフルオロメトキシフェニル]、[6399:2−エトキシ−6−トリフルオロメトキシフェニル]、[6400:2−エトキシ−3−トリフルオロメチルフェニル]、 [6301: 4-Bromo-1-cyclohexenyl], [6302: 4-Bromo-2-cyclohexenyl], [6303: 4-Bromo-3-cyclohexenyl], [6304: 4-Methyl-1-cyclohexenyl] ], [6305: 4-methyl-2-cyclohexenyl], [6306: 4-methyl-3-cyclohexenyl], [6307: 4-ethyl-1-cyclohexenyl], [6308: 4-ethyl-2- Cyclohexenyl], [6309: 4-ethyl-3-cyclohexenyl], [6310: trifluoromethyl], [6311: tert-butyl], [6312: 3-fluoro-2-methoxyphenyl], [6313: 4 -Fluoro-2-methoxyphenyl], [6314: 5-fluoro-2-methoxyphenyl], [6315: 6- [Luoro-2-methoxyphenyl], [6316: 3-chloro-2-methoxyphenyl], [6317: 4-chloro-2-methoxyphenyl], [6318: 5-chloro-2-methoxyphenyl], [6319: 6-chloro-2-methoxyphenyl], [6320: 3-bromo-2-methoxyphenyl], [6321: 4-bromo-2-methoxyphenyl], [6322: 5-bromo-2-methoxyphenyl], [ 6323: 6-Bromo-2-methoxyphenyl], [6324: 3-iodo-2-methoxyphenyl], [6325: 4-iodo-2-methoxyphenyl], [6326: 5-iodo-2-methoxyphenyl] [6327: 6-iodo-2-methoxyphenyl], [6328: 2,3-dimethoxyphenyl], [6329: 2, 4-dimethoxyphenyl], [6330: 2,5-dimethoxyphenyl], [6331: 2,6-dimethoxyphenyl], [6332: 3-methyl-2-methoxyphenyl], [6333: 4-methyl-2- Methoxyphenyl], [6334: 5-methyl-2-methoxyphenyl], [6335: 6-methyl-2-methoxyphenyl], [6336: 3-ethyl-2-methoxyphenyl], [6337: 4-ethyl- 2-methoxyphenyl], [6338: 5-ethyl-2-methoxyphenyl], [6339: 6-ethyl-2-methoxyphenyl], [6340: 3-trifluoromethoxy-2-methoxyphenyl], [6341: 4-trifluoromethoxy-2-methoxyphenyl], [6342: 5-trifluoromethoxy-2-methoxy Phenyl], [6343: 6-trifluoromethoxy-2-methoxyphenyl], [6344: 3-trifluoromethyl-2-methoxyphenyl], [6345: 4-trifluoromethyl-2-methoxyphenyl], [6346 : 5-trifluoromethyl-2-methoxyphenyl], [6347: 6-trifluoromethyl-2-methoxyphenyl], [6348: 3-methylthio-2-methoxyphenyl], [6349: 4-methylthio-2- Methoxyphenyl], [6350: 5-methylthio-2-methoxyphenyl], [6351: 6-methylthio-2-methoxyphenyl], [6352: 3-trifluoromethylthio-2-methoxyphenyl], [6353: 4- Trifluoromethylthio-2-methoxyphenyl], [6354: 5 Trifluoromethylthio-2-methoxyphenyl], [6355: 6-trifluoromethylthio-2-methoxyphenyl], [6356: 3-ethynyl-2-methoxyphenyl], [6357: 4-ethynyl-2-methoxyphenyl] [6358: 5-ethynyl-2-methoxyphenyl], [6359: 6-ethynyl-2-methoxyphenyl], [6360: 3-cyclopropyl-2-methoxyphenyl], [6361: 4-cyclopropyl-2] -Methoxyphenyl], [6362: 5-cyclopropyl-2-methoxyphenyl], [6363: 6-cyclopropyl-2-methoxyphenyl], [6364: 3-cyclopropyloxy-2-methoxyphenyl], [6365 : 4-cyclopropyloxy-2-methoxyphenyl], [63 66: 5-cyclopropyloxy-2-methoxyphenyl], [6367: 6-cyclopropyloxy-2-methoxyphenyl], [6368: 2-ethoxy-3-fluorophenyl], [6369: 2-ethoxy-4. -Fluorophenyl], [6370: 2-ethoxy-5-fluorophenyl], [6331: 2-ethoxy-6-fluorophenyl], [6372: 3-chloro-2-ethoxyphenyl], [6373: 4-chloro. -2-ethoxyphenyl], [6374: 5-chloro-2-ethoxyphenyl], [6375: 6-chloro-2-ethoxyphenyl], [6376: 3-bromo-2-ethoxyphenyl], [6377: 4 -Bromo-2-ethoxyphenyl], [6378: 5-Bromo-2-ethoxyphenyl], [6379: -Bromo-2-ethoxyphenyl], [6380: 2-ethoxy-3-iodophenyl], [6381: 2-ethoxy-4-iodophenyl], [6382: 2-ethoxy-5-iodophenyl], [6383 : 2-ethoxy-6-iodophenyl], [6384: 2,3-diethoxyphenyl], [6385: 2,4-diethoxyphenyl], [6386: 2,5-diethoxyphenyl], [6387: 2,6-diethoxyphenyl], [6388: 2-ethoxy-3-methylphenyl], [6389: 2-ethoxy-4-methylphenyl], [6390: 2-ethoxy-5-methylphenyl], [6381 : 2-ethoxy-6-methylphenyl], [6392: 3-ethyl-2-ethoxyphenyl], [6393: 4-ethyl-2-ethyl Xiphenyl], [6394: 5-ethyl-2-ethoxyphenyl], [6395: 6-ethyl-2-ethoxyphenyl], [6396: 2-ethoxy-3-trifluoromethoxyphenyl], [6397: 2-ethoxy -4-trifluoromethoxyphenyl], [6398: 2-ethoxy-5-trifluoromethoxyphenyl], [6399: 2-ethoxy-6-trifluoromethoxyphenyl], [6400: 2-ethoxy-3-trifluoro. Methylphenyl],
[6401:2−エトキシ−4−トリフルオロメチルフェニル]、[6402:2−エトキシ−5−トリフルオロメチルフェニル]、[6403:2−エトキシ−6−トリフルオロメチルフェニル]、[6404:2−エトキシ−3−メチルチオフェニル]、[6405:2−エトキシ−4−メチルチオフェニル]、[6406:2−エトキシ−5−メチルチオフェニル]、[6407:2−エトキシ−6−メチルチオフェニル]、[6408:2−エトキシ−3−トリフルオロメチルチオフェニル]、[6409:2−エトキシ−4−トリフルオロメチルチオフェニル]、[6410:2−エトキシ−5−トリフルオロメチルチオフェニル]、[6411:2−エトキシ−6−トリフルオロメチルチオフェニル]、[6412:3−エチニル−2−エトキシフェニル]、[6413:4−エチニル−2−エトキシフェニル]、[6414:5−エチニル−2−エトキシフェニル]、[6415:6−エチニル−2−エトキシフェニル]、[6416:3−シクロプロピル−2−エトキシフェニル]、[6417:4−シクロプロピル−2−エトキシフェニル]、[6418:5−シクロプロピル−2−エトキシフェニル]、[6419:6−シクロプロピル−2−エトキシフェニル]、[6420:3−シクロプロピルオキシ−2−エトキシフェニル]、[6421:4−シクロプロピルオキシ−2−エトキシフェニル]、[6422:5−シクロプロピルオキシ−2−エトキシフェニル]、[6423:6−シクロプロピルオキシ−2−エトキシフェニル]、[6424:3−メトキシ−2−メチルフェニル]、[6425:4−メトキシ−2−メチルフェニル]、[6426:5−メトキシ−2−メチルフェニル]、[6427:6−メトキシ−2−メチルフェニル]、[6428:3−エトキシ−2−メチルフェニル]、[6429:4−エトキシ−2−メチルフェニル]、[6430:5−エトキシ−2−メチルフェニル]、[6431:6−エトキシ−2−メチルフェニル]、[6432:3−エチル−2−メチルフェニル]、[6433:4−エチル−2−メチルフェニル]、[6434:5−エチル−2−メチルフェニル]、[6435:6−エチル−2−メチルフェニル]、[6436:3−トリフルオロメトキシ−2−メチルフェニル]、[6437:4−トリフルオロメトキシ−2−メチルフェニル]、[6438:5−トリフルオロメトキシ−2−メチルフェニル]、[6439:6−トリフルオロメトキシ−2−メチルフェニル]、[6440:3−トリフルオロメチル−2−メチルフェニル]、[6441:4−トリフルオロメチル−2−メチルフェニル]、[6442:5−トリフルオロメチル−2−メチルフェニル]、[6443:6−トリフルオロメチル−2−メチルフェニル]、[6444:3−メチルチオ−2−メチルフェニル]、[6445:4−メチルチオ−2−メチルフェニル]、[6446:5−メチルチオ−2−メチルフェニル]、[6447:6−メチルチオ−2−メチルフェニル]、[6448:4−フルオロ−2−イソプロピルオキシフェニル]、[6449:4−クロロ−2−イソプロピルオキシフェニル]、[6450:4−ブロモ−2−イソプロピルオキシフェニル]、[6451:4−ヨード−2−イソプロピルオキシフェニル]、[6452:4−メチル−2−イソプロピルオキシフェニル]、[6453:4−エチル−2−イソプロピルオキシフェニル]、[6454:4−メトキシ−2−イソプロピルオキシフェニル]、[6455:4−エトキシ−2−イソプロピルオキシフェニル]、[6456:4−トリフルオロメチル−2−イソプロピルオキシフェニル]、[6457:4−トリフルオロメトキシ−2−イソプロピルオキシフェニル]、[6458:4−メチルチオ−2−イソプロピルオキシフェニル]、[6459:4−シクロプロピル−2−イソプロピルオキシフェニル]、[6460:4−フルオロ−2−シクロプロピルオキシフェニル]、[6461:4−クロロ−2−シクロプロピルオキシフェニル]、[6462:4−ブロモ−2−シクロプロピルオキシフェニル]、[6463:4−ヨード−2−シクロプロピルオキシフェニル]、[6464:4−メチル−2−シクロプロピルオキシフェニル]、[6465:4−エチル−2−シクロプロピルオキシフェニル]、[6466:4−メトキシ−2−シクロプロピルオキシフェニル]、[6467:4−エトキシ−2−シクロプロピルオキシフェニル]、[6468:4−トリフルオロメチル−2−シクロプロピルオキシフェニル]、[6469:4−トリフルオロメトキシ−2−シクロプロピルオキシフェニル]、[6470:4−メチルチオ−2−シクロプロピルオキシフェニル]、[6471:4−シクロプロピル−2−シクロプロピルオキシフェニル]、[6472:3,4−ジフルオロ−2−メトキシフェニル]、[6473:4,5−ジフルオロ−2−メトキシフェニル]、[6474:4,6−ジフルオロ−2−メトキシフェニル]、[6475:3,4,5−トリフルオロ−2−メトキシフェニル]、[6476:3,4,5,6−テトラフルオロ−2−メトキシフェニル]、[6477:4−クロロ−3−フルオロ−2−メトキシフェニル]、[6478:4−クロロ−5−フルオロ−2−メトキシフェニル]、[6479:4−クロロ−6−フルオロ−2−メトキシフェニル]、[6480:4−ブロモ−3−フルオロ−2−メトキシフェニル]、[6481:4−ブロモ−5−フルオロ−2−メトキシフェニル]、[6482:4−ブロモ−6−フルオロ−2−メトキシフェニル]、[6483:3,4−ジフルオロ−2−エトキシフェニル]、[6484:4,5−ジフルオロ−2−エトキシフェニル]、[6485:4,6−ジフルオロ−2−エトキシフェニル]、[6486:3,4,5−トリフルオロ−2−エトキシフェニル]、[6487:3,4,5,6−テトラフルオロ−2−エトキシフェニル]、[6488:4−クロロ−3−フルオロ−2−エトキシフェニル]、[6489:4−クロロ−5−フルオロ−2−エトキシフェニル]、[6490:4−クロロ−6−フルオロ−2−エトキシフェニル]、[6491:4−ブロモ−3−フルオロ−2−エトキシフェニル]、[6492:4−ブロモ−5−フルオロ−2−エトキシフェニル]、[6493:4−ブロモ−6−フルオロ−2−エトキシフェニル]、[6494:3,4−ジフルオロ−2−イソプロピルオキシフェニル]、[6495:4,5−ジフルオロ−2−イソプロピルオキシフェニル]、[6496:4,6−ジフルオロ−2−イソプロピルオキシフェニル]、[6497:3,4,5−トリフルオロ−2−イソプロピルオキシフェニル]、[6498:3,4,5,6−テトラフルオロ−2−イソプロピルオキシフェニル]、[6499:4−クロロ−3−フルオロ−2−イソプロピルオキシフェニル]、[6500:4−クロロ−5−フルオロ−2−イソプロピルオキシフェニル]、 [6401: 2-ethoxy-4-trifluoromethylphenyl], [6402: 2-ethoxy-5-trifluoromethylphenyl], [6403: 2-ethoxy-6-trifluoromethylphenyl], [6404: 2- Ethoxy-3-methylthiophenyl], [6405: 2-ethoxy-4-methylthiophenyl], [6406: 2-ethoxy-5-methylthiophenyl], [6407: 2-ethoxy-6-methylthiophenyl], [6408: 2-ethoxy-3-trifluoromethylthiophenyl], [6409: 2-ethoxy-4-trifluoromethylthiophenyl], [6410: 2-ethoxy-5-trifluoromethylthiophenyl], [6411: 2-ethoxy-6 -Trifluoromethylthiophenyl], [6412: 3-ethini -2-ethoxyphenyl], [6413: 4-ethynyl-2-ethoxyphenyl], [6414: 5-ethynyl-2-ethoxyphenyl], [6415: 6-ethynyl-2-ethoxyphenyl], [6416: 3 -Cyclopropyl-2-ethoxyphenyl], [6417: 4-cyclopropyl-2-ethoxyphenyl], [6418: 5-cyclopropyl-2-ethoxyphenyl], [6419: 6-cyclopropyl-2-ethoxyphenyl] ], [6420: 3-cyclopropyloxy-2-ethoxyphenyl], [6421: 4-cyclopropyloxy-2-ethoxyphenyl], [6422: 5-cyclopropyloxy-2-ethoxyphenyl], [6423: 6-cyclopropyloxy-2-ethoxyphenyl], [6424: 3- Toxi-2-methylphenyl], [6425: 4-methoxy-2-methylphenyl], [6426: 5-methoxy-2-methylphenyl], [6427: 6-methoxy-2-methylphenyl], [6428: 3-ethoxy-2-methylphenyl], [6429: 4-ethoxy-2-methylphenyl], [6430: 5-ethoxy-2-methylphenyl], [6431: 6-ethoxy-2-methylphenyl], [ 6432: 3-ethyl-2-methylphenyl], [6433: 4-ethyl-2-methylphenyl], [6434: 5-ethyl-2-methylphenyl], [6435: 6-ethyl-2-methylphenyl] [6436: 3-trifluoromethoxy-2-methylphenyl], [6437: 4-trifluoromethoxy-2-methylphenyl] ], [6438: 5-trifluoromethoxy-2-methylphenyl], [6439: 6-trifluoromethoxy-2-methylphenyl], [6440: 3-trifluoromethyl-2-methylphenyl], [6441: 4-trifluoromethyl-2-methylphenyl], [6442: 5-trifluoromethyl-2-methylphenyl], [6443: 6-trifluoromethyl-2-methylphenyl], [6444: 3-methylthio-2 -Methylphenyl], [6445: 4-methylthio-2-methylphenyl], [6446: 5-methylthio-2-methylphenyl], [6447: 6-methylthio-2-methylphenyl], [6448: 4-fluoro. -2-isopropyloxyphenyl], [6449: 4-chloro-2-isopropyloxyphene [6450: 4-bromo-2-isopropyloxyphenyl], [6451: 4-iodo-2-isopropyloxyphenyl], [6452: 4-methyl-2-isopropyloxyphenyl], [6453: 4- Ethyl-2-isopropyloxyphenyl], [6454: 4-methoxy-2-isopropyloxyphenyl], [6455: 4-ethoxy-2-isopropyloxyphenyl], [6456: 4-trifluoromethyl-2-isopropyloxy. Phenyl], [6457: 4-trifluoromethoxy-2-isopropyloxyphenyl], [6458: 4-methylthio-2-isopropyloxyphenyl], [6459: 4-cyclopropyl-2-isopropyloxyphenyl], [6460 : 4-Fluoro-2-cyclo [Ropyloxyphenyl], [6461: 4-chloro-2-cyclopropyloxyphenyl], [6462: 4-bromo-2-cyclopropyloxyphenyl], [6463: 4-iodo-2-cyclopropyloxyphenyl] [6464: 4-methyl-2-cyclopropyloxyphenyl], [6465: 4-ethyl-2-cyclopropyloxyphenyl], [6466: 4-methoxy-2-cyclopropyloxyphenyl], [6467: 4. -Ethoxy-2-cyclopropyloxyphenyl], [6468: 4-trifluoromethyl-2-cyclopropyloxyphenyl], [6469: 4-trifluoromethoxy-2-cyclopropyloxyphenyl], [6470: 4- Methylthio-2-cyclopropyloxyphenyl], [647 1: 4-cyclopropyl-2-cyclopropyloxyphenyl], [6472: 3,4-difluoro-2-methoxyphenyl], [6473: 4,5-difluoro-2-methoxyphenyl], [6474: 4 6-difluoro-2-methoxyphenyl], [6475: 3,4,5-trifluoro-2-methoxyphenyl], [6476: 3,4,5,6-tetrafluoro-2-methoxyphenyl], [6477 : 4-chloro-3-fluoro-2-methoxyphenyl], [6478: 4-chloro-5-fluoro-2-methoxyphenyl], [6479: 4-chloro-6-fluoro-2-methoxyphenyl], [ 6480: 4-bromo-3-fluoro-2-methoxyphenyl], [6481: 4-bromo-5-fluoro-2-methoxyphenyl] [6482: 4-Bromo-6-fluoro-2-methoxyphenyl], [6483: 3,4-difluoro-2-ethoxyphenyl], [6484: 4,5-difluoro-2-ethoxyphenyl], [6485: 4,6-difluoro-2-ethoxyphenyl], [6486: 3,4,5-trifluoro-2-ethoxyphenyl], [6487: 3,4,5,6-tetrafluoro-2-ethoxyphenyl], [6488: 4-chloro-3-fluoro-2-ethoxyphenyl], [6489: 4-chloro-5-fluoro-2-ethoxyphenyl], [6490: 4-chloro-6-fluoro-2-ethoxyphenyl] [6491: 4-Bromo-3-fluoro-2-ethoxyphenyl], [6492: 4-Bromo-5-fluoro-2-ethoxypheny]. ], [6493: 4-Bromo-6-fluoro-2-ethoxyphenyl], [6494: 3,4-difluoro-2-isopropyloxyphenyl], [6495: 4,5-difluoro-2-isopropyloxyphenyl] [6496: 4,6-difluoro-2-isopropyloxyphenyl], [6497: 3,4,5-trifluoro-2-isopropyloxyphenyl], [6498: 3,4,5,6-tetrafluoro- 2-isopropyloxyphenyl], [6499: 4-chloro-3-fluoro-2-isopropyloxyphenyl], [6500: 4-chloro-5-fluoro-2-isopropyloxyphenyl],
[6501:4−クロロ−6−フルオロ−2−イソプロピルオキシフェニル]、[6502:4−ブロモ−3−フルオロ−2−イソプロピルオキシフェニル]、[6503:4−ブロモ−5−フルオロ−2−イソプロピルオキシフェニル]、[6504:4−ブロモ−6−フルオロ−2−イソプロピルオキシフェニル]、[6505:3,4−ジフルオロ−2−シクロプロピルオキシフェニル]、[6506:4,5−ジフルオロ−2−シクロプロピルオキシフェニル]、[6507:4,6−ジフルオロ−2−シクロプロピルオキシフェニル]、[6508:3,4,5−トリフルオロ−2−シクロプロピルオキシフェニル]、[6509:3,4,5,6−テトラフルオロ−2−シクロプロピルオキシフェニル]、[6510:4−クロロ−3−フルオロ−2−シクロプロピルオキシフェニル]、[6511:4−クロロ−5−フルオロ−2−シクロプロピルオキシフェニル]、[6512:4−クロロ−6−フルオロ−2−シクロプロピルオキシシフェニル]、[6513:4−ブロモ−3−フルオロ−2−シクロプロピルオキシフェニル]、[6514:4−ブロモ−5−フルオロ−2−シクロプロピルオキシシフェニル]、[6515:4−ブロモ−6−フルオロ−2−シクロプロピルオキシフェニル]、[6516:3−エチニル−2−メチルフェニル]、[6517:4−エチニル−2−メチルフェニル]、[6518:5−エチニル−2−メチルフェニル]、[6519:6−エチニル−2−メチルフェニル]、[6520:3−シクロプロピル−2−メチルフェニル]、[6521:4−シクロプロピル−2−メチルフェニル]、[6522:5−シクロプロピル−2−メチルフェニル]、[6523:6−シクロプロピル−2−メチルフェニル]、[6524:3−シクロプロピルオキシ−2−メチルフェニル]、[6525:4−シクロプロピルオキシ−2−メチルフェニル]、[6526:5−シクロプロピルオキシ−2−メチルフェニル]、[6527:6−シクロプロピルオキシ−2−メチルフェニル]、[6528:3−メトキシ−2−フルオロフェニル]、[6529:4−メトキシ−2−フルオロフェニル]、[6530:5−メトキシ−2−フルオロフェニル]、[6531:6−メトキシ−2−フルオロフェニル]、[6532:3−エトキシ−2−フルオロフェニル]、[6533:4−エトキシ−2−フルオロフェニル]、[6534:5−エトキシ−2−フルオロフェニル]、[6535:6−エトキシ−2−フルオロフェニル]、[6536:3−エチル−2−フルオロフェニル]、[6537:5−エチル−2−フルオロフェニル]、[6538:6−エチル−2−フルオロフェニル]、[6539:2−フルオロ−3−トリフルオロメトキシフェニル]、[6540:2−フルオロ−4−トリフルオロメトキシフェニル]、[6541:2−フルオロ−5−トリフルオロメトキシフェニル]、[6542:2−フルオロ−6−トリフルオロメトキシフェニル]、[6543:2−フルオロ−3−トリフルオロメチルフェニル]、[6544:2−フルオロ−4−トリフルオロメチルフェニル]、[6545:2−フルオロ−5−トリフルオロメチルフェニル]、[6546:2−フルオロ−6−トリフルオロメチルフェニル]、[6547:2−フルオロ−3−フルオロチオフェニル]、[6548:2−フルオロ−4−フルオロチオフェニル]、[6549:2−フルオロ−5−フルオロチオフェニル]、[6550:2−フルオロ−6−フルオロチオフェニル]、[6551:3−エチニル−2−フルオロフェニル]、[6552:4−エチニル−2−フルオロフェニル]、[6553:5−エチニル−2−フルオロフェニル]、[6554:6−エチニル−2−フルオロフェニル]、[6555:3−シクロプロピル−2−フルオロフェニル]、[6556:4−シクロプロピル−2−フルオロフェニル]、[6557:5−シクロプロピル−2−フルオロフェニル]、[6558:6−シクロプロピル−2−フルオロフェニル]、[6559:3−シクロプロピルオキシ−2−フルオロフェニル]、[6560:4−シクロプロピルオキシ−2−フルオロフェニル]、[6561:5−シクロプロピルオキシ−2−フルオロフェニル]、[6562:6−シクロプロピルオキシ−2−フルオロフェニル]、[6563:2−エチル−3−フルオロフェニル]、[6564:2−エチル−4−フルオロフェニル]、[6565:2−エチル−5−フルオロフェニル]、[6566:2−エチル−6−フルオロフェニル]、[6567:3−クロロ−2−エチルフェニル]、[6568:4−クロロ−2−エチルフェニル]、[6569:5−クロロ−2−エチルフェニル]、[6570:6−クロロ−2−エチルフェニル]、[6571:3−ブロモ−2−エチルフェニル]、[6572:4−ブロモ−2−エチルフェニル]、[6573:5−ブロモ−2−エチルフェニル]、[6574:6−ブロモ−2−エチルフェニル]、[6575:2−エチル−3−ヨードフェニル]、[6576:2−エチル−4−ヨードフェニル]、[6577:2−エチル−5−ヨードフェニル]、[6578:2−エチル−6−ヨードフェニル]、[6579:2−エチル−3−エトキシフェニル]、[6580:2−エチル−4−エトキシフェニル]、[6581:2−エチル−5−エトキシフェニル]、[6582:2−エチル−6−エトキシフェニル]、[6583:2−エチル−3−メチルフェニル]、[6584:2−エチル−4−メチルフェニル]、[6585:2−エチル−5−メチルフェニル]、[6586:2−エチル−6−メチルフェニル]、[6587:2,3−ジエチルフェニル]、[6588:2,4−ジエチルフェニル]、[6589:2,5−ジエチルフェニル]、[6590:2,6−ジエチルフェニル]、[6591:2−エチル−3−トリフルオロメトキシフェニル]、[6592:2−エチル−4−トリフルオロメトキシフェニル]、[6593:2−エチル−5−トリフルオロメトキシフェニル]、[6594:2−エチル−6−トリフルオロメトキシフェニル]、[6595:2−エチル−3−トリフルオロメチルフェニル]、[6596:2−エチル−4−トリフルオロメチルフェニル]、[6597:2−エチル−5−トリフルオロメチルフェニル]、[6598:2−エチル−6−トリフルオロメチルフェニル]、[6599:2−エチル−3−メチルチオフェニル]、[6600:2−エチル−4−メチルチオフェニル]、 [6501: 4-Chloro-6-fluoro-2-isopropyloxyphenyl], [6502: 4-Bromo-3-fluoro-2-isopropyloxyphenyl], [6503: 4-Bromo-5-fluoro-2-isopropyl Oxyphenyl], [6504: 4-bromo-6-fluoro-2-isopropyloxyphenyl], [6505: 3,4-difluoro-2-cyclopropyloxyphenyl], [6506: 4,5-difluoro-2- Cyclopropyloxyphenyl], [6507: 4,6-difluoro-2-cyclopropyloxyphenyl], [6508: 3,4,5-trifluoro-2-cyclopropyloxyphenyl], [6509: 3,4, 5,6-tetrafluoro-2-cyclopropyloxyphenyl], [6510: 4-chloro -3-fluoro-2-cyclopropyloxyphenyl], [6511: 4-chloro-5-fluoro-2-cyclopropyloxyphenyl], [6512: 4-chloro-6-fluoro-2-cyclopropyloxyphenyl] ], [6513: 4-Bromo-3-fluoro-2-cyclopropyloxyphenyl], [6514: 4-Bromo-5-fluoro-2-cyclopropyloxyphenyl], [6515: 4-Bromo-6- Fluoro-2-cyclopropyloxyphenyl], [6516: 3-ethynyl-2-methylphenyl], [6517: 4-ethynyl-2-methylphenyl], [6518: 5-ethynyl-2-methylphenyl], [ 6519: 6-ethynyl-2-methylphenyl], [6520: 3-cyclopropyl-2-methylphen [6521: 4-cyclopropyl-2-methylphenyl], [6522: 5-cyclopropyl-2-methylphenyl], [6523: 6-cyclopropyl-2-methylphenyl], [6524: 3- Cyclopropyloxy-2-methylphenyl], [6525: 4-cyclopropyloxy-2-methylphenyl], [6526: 5-cyclopropyloxy-2-methylphenyl], [6527: 6-cyclopropyloxy-2] -Methylphenyl], [6528: 3-methoxy-2-fluorophenyl], [6529: 4-methoxy-2-fluorophenyl], [6530: 5-methoxy-2-fluorophenyl], [6531: 6-methoxy -2-fluorophenyl], [6532: 3-ethoxy-2-fluorophenyl], [653 3: 4-ethoxy-2-fluorophenyl], [6534: 5-ethoxy-2-fluorophenyl], [6535: 6-ethoxy-2-fluorophenyl], [6536: 3-ethyl-2-fluorophenyl] , [6537: 5-ethyl-2-fluorophenyl], [6538: 6-ethyl-2-fluorophenyl], [6539: 2-fluoro-3-trifluoromethoxyphenyl], [6540: 2-fluoro-4 -Trifluoromethoxyphenyl], [6541: 2-fluoro-5-trifluoromethoxyphenyl], [6542: 2-fluoro-6-trifluoromethoxyphenyl], [6543: 2-fluoro-3-trifluoromethylphenyl] ], [6544: 2-Fluoro-4-trifluoromethylphenyl], [6545: -Fluoro-5-trifluoromethylphenyl], [6546: 2-fluoro-6-trifluoromethylphenyl], [6547: 2-fluoro-3-fluorothiophenyl], [6548: 2-fluoro-4-fluoro. Thiophenyl], [6549: 2-fluoro-5-fluorothiophenyl], [6550: 2-fluoro-6-fluorothiophenyl], [6551: 3-ethynyl-2-fluorophenyl], [6552: 4- [Ethynyl-2-fluorophenyl], [6553: 5-ethynyl-2-fluorophenyl], [6554: 6-ethynyl-2-fluorophenyl], [6555: 3-cyclopropyl-2-fluorophenyl], [6556] : 4-cyclopropyl-2-fluorophenyl], [6557: 5-cyclopropyl. 2-fluorophenyl], [6558: 6-cyclopropyl-2-fluorophenyl], [6559: 3-cyclopropyloxy-2-fluorophenyl], [6560: 4-cyclopropyloxy-2-fluorophenyl], [6561: 5-cyclopropyloxy-2-fluorophenyl], [6562: 6-cyclopropyloxy-2-fluorophenyl], [6563: 2-ethyl-3-fluorophenyl], [6564: 2-ethyl- 4-fluorophenyl], [6565: 2-ethyl-5-fluorophenyl], [6566: 2-ethyl-6-fluorophenyl], [6567: 3-chloro-2-ethylphenyl], [6568: 4- Chloro-2-ethylphenyl], [6569: 5-chloro-2-ethylphenyl], [657 0: 6-chloro-2-ethylphenyl], [6571: 3-bromo-2-ethylphenyl], [6572: 4-bromo-2-ethylphenyl], [6573: 5-bromo-2-ethylphenyl] [6574: 6-bromo-2-ethylphenyl], [6575: 2-ethyl-3-iodophenyl], [6576: 2-ethyl-4-iodophenyl], [6577: 2-ethyl-5-iodo. Phenyl], [6578: 2-ethyl-6-iodophenyl], [6579: 2-ethyl-3-ethoxyphenyl], [6580: 2-ethyl-4-ethoxyphenyl], [6581: 2-ethyl-5 -Ethoxyphenyl], [6582: 2-ethyl-6-ethoxyphenyl], [6583: 2-ethyl-3-methylphenyl], [6584: 2-ethyl. 4-methylphenyl], [6585: 2-ethyl-5-methylphenyl], [6586: 2-ethyl-6-methylphenyl], [6587: 2,3-diethylphenyl], [6588: 2,4- Diethylphenyl], [6589: 2,5-diethylphenyl], [6590: 2,6-diethylphenyl], [6591: 2-ethyl-3-trifluoromethoxyphenyl], [6592: 2-ethyl-4- Trifluoromethoxyphenyl], [6593: 2-ethyl-5-trifluoromethoxyphenyl], [6594: 2-ethyl-6-trifluoromethoxyphenyl], [6595: 2-ethyl-3-trifluoromethylphenyl]. [6596: 2-ethyl-4-trifluoromethylphenyl], [6597: 2-ethyl-5-trifluoro. Oro-methylphenyl], [6598: 2-ethyl-6-trifluoromethyl-phenyl], [6599: 2-ethyl-3-methylthiophenyl], [6600: 2-ethyl-4-methylthiophenyl,
[6601:2−エチル−5−メチルチオフェニル]、[6602:2−エチル−6−メチルチオフェニル]、[6603:2−エチル−3−トリフルオロメチルチオフェニル]、[6604:2−エチル−4−トリフルオロメチルチオフェニル]、[6605:2−エチル−5−トリフルオロメチルチオフェニル]、[6606:2−エチル−6−トリフルオロメチルチオフェニル]、[6607:3−エチニル−2−エチルフェニル]、[6608:4−エチニル−2−エチルフェニル]、[6609:5−エチニル−2−エチルフェニル]、[6610:6−エチニル−2−エチルフェニル]、[6611:3−シクロプロピル−2−エチルフェニル]、[6612:4−シクロプロピル−2−エチルフェニル]、[6613:5−シクロプロピル−2−エチルフェニル]、[6614:6−シクロプロピル−2−エチルフェニル]、[6615:3−シクロプロピルオキシ−2−エチルフェニル]、[6616:4−シクロプロピルオキシ−2−エチルフェニル]、[6617:5−シクロプロピルオキシ−2−エチルフェニル]、[6618:6−シクロプロピルオキシ−2−エチルフェニル]、[6619:3−フルオロ−2−トリフルオロメチルフェニル]、[6620:4−フルオロ−2−トリフルオロメチルフェニル]、[6621:5−フルオロ−2−トリフルオロメチルフェニル]、[6622:6−フルオロ−2−トリフルオロメチルフェニル]、[6623:3−クロロ−2−トリフルオロメチルフェニル]、[6624:4−クロロ−2−トリフルオロメチルフェニル]、[6625:5−クロロ−2−トリフルオロメチルフェニル]、[6626:6−クロロ−2−トリフルオロメチルフェニル]、[6627:3−ブロモ−2−トリフルオロメチルフェニル]、[6628:4−ブロモ−2−トリフルオロメチルフェニル]、[6629:5−ブロモ−2−トリフルオロメチルフェニル]、[6630:6−ブロモ−2−トリフルオロメチルフェニル]、[6631:3−ヨード−2−トリフルオロメチルフェニル]、[6632:4−ヨード−2−トリフルオロメチルフェニル]、[6633:5−ヨード−2−トリフルオロメチルフェニル]、[6634:6−ヨード−2−トリフルオロメチルフェニル]、[6635:3−エトキシ−2−トリフルオロメチルフェニル]、[6636:4−エトキシ−2−トリフルオロメチルフェニル]、[6637:5−エトキシ−2−トリフルオロメチルフェニル]、[6638:6−エトキシ−2−トリフルオロメチルフェニル]、[6639:3−メチル−2−トリフルオロメチルフェニル]、[6640:4−メチル−2−トリフルオロメチルフェニル]、[6641:5−メチル−2−トリフルオロメチルフェニル]、[6642:6−メチル−2−トリフルオロメチルフェニル]、[6643:2,3−ジトリフルオロメチルフェニル]、[6644:2,4−ジトリフルオロメチルフェニル]、[6645:2,5−ジトリフルオロメチルフェニル]、[6646:2,6−ジトリフルオロメチルフェニル]、[6647:2−トリフルオロメチル−3−トリフルオロメトキシフェニル]、[6648:2−トリフルオロメチル−4−トリフルオロメトキシフェニル]、[6649:2−トリフルオロメチル−5−トリフルオロメトキシフェニル]、[6650:2−トリフルオロメチル−6−トリフルオロメトキシフェニル]、[6651:2−エチル−3−トリフルオロメチルフェニル]、[6652:2−エチル−4−トリフルオロメチルフェニル]、[6653:2−エチル−5−トリフルオロメチルフェニル]、[6654:2−エチル−6−トリフルオロメチルフェニル]、[6655:3−メチルチオ−2−トリフルオロメチルフェニル]、[6656:4−メチルチオ−2−トリフルオロメチルフェニル]、[6657:5−メチルチオ−2−トリフルオロメチルフェニル]、[6658:6−メチルチオ−2−トリフルオロメチルフェニル]、[6659:2−トリフルオロメチル−3−トリフルオロメチルチオフェニル]、[6660:2−トリフルオロメチル−4−トリフルオロメチルチオフェニル]、[6661:2−トリフルオロメチル−5−トリフルオロメチルチオフェニル]、[6662:2−トリフルオロメチル−6−トリフルオロメチルチオフェニル]、[6663:3−エチニル−2−トリフルオロメチルフェニル]、[6664:4−エチニル−2−トリフルオロメチルフェニル]、[6665:5−エチニル−2−トリフルオロメチルフェニル]、[6666:6−エチニル−2−トリフルオロメチルフェニル]、[6667:3−シクロプロピル−2−トリフルオロメチルフェニル]、[6668:4−シクロプロピル−2−トリフルオロメチルフェニル]、[6669:5−シクロプロピル−2−トリフルオロメチルフェニル]、[6670:6−シクロプロピル−2−トリフルオロメチルフェニル]、[6671:3−シクロプロピルオキシ−2−トリフルオロメチルフェニル]、[6672:4−シクロプロピルオキシ−2−トリフルオロメチルフェニル]、[6673:5−シクロプロピルオキシ−2−トリフルオロメチルフェニル]、[6674:6−シクロプロピルオキシ−2−トリフルオロメチルフェニル]、[6675:3−メトキシナフタレン−2−イル]、[6676:6−クロロ−3−メトキシナフタレン−2−イル]、[6677:6−フルオロ−3−メトキシナフタレン−2−イル]、[6678:7−クロロ−3−メトキシナフタレン−2−イル]、[6679:7−フルオロ−3−メトキシナフタレン−2−イル]、[6680:8−クロロ−3−メトキシナフタレン−2−イル]、[6681:8−フルオロ−3−メトキシナフタレン−2−イル]、[6682:1−クロロ−3−メトキシナフタレン−2−イル]、[6683:1−フルオロ−3−メトキシナフタレン−2−イル]、[6684:4−クロロ−3−メトキシナフタレン−2−イル]、[6685:4−フルオロ−3−メトキシナフタレン−2−イル]、[6686:5−クロロ−3−メトキシナフタレン−2−イル]、[6687:5−フルオロ−3−メトキシナフタレン−2−イル]、[6688:1−ナフチル]、[6689:2−ナフチル]、[6690:アダマンタン−1−イル]、[6691:3−メチルアダマンタン−1−イル]、[6692:5−メチルアダマンタン−1−イル]、[6693:5,7−ジメチルアダマンタン−1−イル]、[6694:3,5−ジメチルアダマンタン−1−イル]、[6695:3,5,7−トリメチルアダマンタン−1−イル]、[6696:5−メチルアダマンタン−1−イル]、[6697:5,7−ジメチルアダマンタン−1−イル]、[6698:3,5−ジメチルアダマンタン−1−イル]、[6699:3,5,7−トリメチルアダマンタン−1−イル]、[6700:PYR1]、 [6601: 2-ethyl-5-methylthiophenyl], [6602: 2-ethyl-6-methylthiophenyl], [6603: 2-ethyl-3-trifluoromethylthiophenyl], [6604: 2-ethyl-4- Trifluoromethylthiophenyl], [6605: 2-ethyl-5-trifluoromethylthiophenyl], [6606: 2-ethyl-6-trifluoromethylthiophenyl], [6607: 3-ethynyl-2-ethylphenyl], [ 6608: 4-ethynyl-2-ethylphenyl], [6609: 5-ethynyl-2-ethylphenyl], [6610: 6-ethynyl-2-ethylphenyl], [6611: 3-cyclopropyl-2-ethylphenyl] ], [6612: 4-Cyclopropyl-2-ethylphenyl], [6613: 5-Si Ropropyl-2-ethylphenyl], [6614: 6-cyclopropyl-2-ethylphenyl], [6615: 3-cyclopropyloxy-2-ethylphenyl], [6616: 4-cyclopropyloxy-2-ethylphenyl] ], [6617: 5-cyclopropyloxy-2-ethylphenyl], [6618: 6-cyclopropyloxy-2-ethylphenyl], [6619: 3-fluoro-2-trifluoromethylphenyl], [6620: 4-fluoro-2-trifluoromethylphenyl], [6621: 5-fluoro-2-trifluoromethylphenyl], [6622: 6-fluoro-2-trifluoromethylphenyl], [6623: 3-chloro-2 -Trifluoromethylphenyl], [6624: 4-chloro-2-trifluoro Methylphenyl], [6625: 5-chloro-2-trifluoromethylphenyl], [6626: 6-chloro-2-trifluoromethylphenyl], [6627: 3-bromo-2-trifluoromethylphenyl], [ 6628: 4-bromo-2-trifluoromethylphenyl], [6629: 5-bromo-2-trifluoromethylphenyl], [6630: 6-bromo-2-trifluoromethylphenyl], [6631: 3-iodo -2-trifluoromethylphenyl], [6632: 4-iodo-2-trifluoromethylphenyl], [6633: 5-iodo-2-trifluoromethylphenyl], [6634: 6-iodo-2-trifluoro Methylphenyl], [6635: 3-ethoxy-2-trifluoromethylphenyl], [663 6: 4-Ethoxy-2-trifluoromethylphenyl], [6637: 5-Ethoxy-2-trifluoromethylphenyl], [6638: 6-Ethoxy-2-trifluoromethylphenyl], [6639: 3-Methyl -2-trifluoromethylphenyl], [6640: 4-methyl-2-trifluoromethylphenyl], [6641: 5-methyl-2-trifluoromethylphenyl], [6642: 6-methyl-2-trifluoro Methylphenyl], [6643: 2,3-ditrifluoromethylphenyl], [6644: 2,4-ditrifluoromethylphenyl], [6665: 2,5-ditrifluoromethylphenyl], [6646: 2,6- Ditrifluoromethylphenyl], [6647: 2-trifluoromethyl-3-trifluorome Xiphenyl], [6648: 2-trifluoromethyl-4-trifluoromethoxyphenyl], [6649: 2-trifluoromethyl-5-trifluoromethoxyphenyl], [6650: 2-trifluoromethyl-6-trifluoro Methoxyphenyl], [6651: 2-ethyl-3-trifluoromethylphenyl], [6652: 2-ethyl-4-trifluoromethylphenyl], [6653: 2-ethyl-5-trifluoromethylphenyl], [ 6654: 2-ethyl-6-trifluoromethylphenyl], [6655: 3-methylthio-2-trifluoromethylphenyl], [6656: 4-methylthio-2-trifluoromethylphenyl], [6657: 5-methylthio -2-trifluoromethylphenyl], [6658: 6 Methylthio-2-trifluoromethylphenyl], [6659: 2-trifluoromethyl-3-trifluoromethylthiophenyl], [6660: 2-trifluoromethyl-4-trifluoromethylthiophenyl], [6661: 2-tri Fluoromethyl-5-trifluoromethylthiophenyl], [6662: 2-trifluoromethyl-6-trifluoromethylthiophenyl], [6663: 3-ethynyl-2-trifluoromethylphenyl], [6664: 4-ethynyl- 2-trifluoromethylphenyl], [6665: 5-ethynyl-2-trifluoromethylphenyl], [6666: 6-ethynyl-2-trifluoromethylphenyl], [6667: 3-cyclopropyl-2-trifluoro Methylphenyl], [6668: 4-si Chloropropyl-2-trifluoromethylphenyl], [6669: 5-cyclopropyl-2-trifluoromethylphenyl], [6670: 6-cyclopropyl-2-trifluoromethylphenyl], [6671: 3-cyclopropyl Oxy-2-trifluoromethylphenyl], [6672: 4-cyclopropyloxy-2-trifluoromethylphenyl], [6673: 5-cyclopropyloxy-2-trifluoromethylphenyl], [6674: 6-cyclo Propyloxy-2-trifluoromethylphenyl], [6675: 3-methoxynaphthalen-2-yl], [6676: 6-chloro-3-methoxynaphthalen-2-yl], [6677: 6-fluoro-3- Methoxynaphthalen-2-yl], [6678: 7-chloro-3- Toxinaphthalen-2-yl], [6679: 7-fluoro-3-methoxynaphthalen-2-yl], [6680: 8-chloro-3-methoxynaphthalen-2-yl], [6681: 8-fluoro-3 -Methoxynaphthalen-2-yl], [6682: 1-chloro-3-methoxynaphthalen-2-yl], [6683: 1-fluoro-3-methoxynaphthalen-2-yl], [6684: 4-chloro- 3-methoxynaphthalen-2-yl], [6685: 4-fluoro-3-methoxynaphthalen-2-yl], [6686: 5-chloro-3-methoxynaphthalen-2-yl], [6687: 5-fluoro -3-methoxynaphthalen-2-yl], [6688: 1-naphthyl], [6689: 2-naphthyl], [6690: adamantane-1 Yl], [6691: 3-methyladamantan-1-yl], [6692: 5-methyladamantan-1-yl], [6693: 5,7-dimethyladamantan-1-yl], [6694: 3,5 -Dimethyladamantan-1-yl], [6695: 3,5,7-trimethyladamantan-1-yl], [6696: 5-methyladamantan-1-yl], [6697: 5,7-dimethyladamantane-1 -Yl], [6698: 3,5-dimethyladamantan-1-yl], [6699: 3,5,7-trimethyladamantan-1-yl], [6700: PYR1],
[6701:3−Me−PYR1]、[6702:3−Me−4−F−PYR1]、[6703:3−Me−4−Cl−PYR1]、[6704:3−Me−4−Br−PYR1]、[6705:3−Me−4−Me−PYR1]、[6706:3−Me−4−Et−PYR1]、[6707:3−Me−4−OMe−PYR1]、[6708:3−Me−4−OEt−PYR1]、[6709:3−Me−4−CN−PYR1]、[6710:3−Me−4−c−Pr−PYR1]、[6711:3−Me−4−CHF2−PYR1]、[6712:3−Me−4−CF3−PYR1]、[6713:3−Me−5−F−PYR1]、[6714:3−Me−4−F−5−F−PYR1]、[6715:3−Me−4−Cl−5−F−PYR1]、[6716:3−Me−4−Br−5−F−PYR1]、[6717:3−Me−4−Me−5−F−PYR1]、[6718:3−Me−4−Et−5−F−PYR1]、[6719:3−Me−4−OMe−5−F−PYR1]、[6720:3−Me−4−OEt−5−F−PYR1]、[6721:3−Me−4−CN−5−F−PYR1]、[6722:3−Me−4−c−Pr−5−F−PYR1]、[6723:3−Me−4−CHF2−5−F−PYR1]、[6724:3−Me−4−CF3−5−F−PYR1]、[6725:3−Me−5−Cl−PYR1]、[6726:3−Me−4−F−5−Cl−PYR1]、[6727:3−Me−4−Cl−5−Cl−PYR1]、[6728:3−Me−4−Br−5−Cl−PYR1]、[6729:3−Me−4−Me−5−Cl−PYR1]、[6730:3−Me−4−Et−5−Cl−PYR1]、[6731:3−Me−4−OMe−5−Cl−PYR1]、[6732:3−Me−4−OEt−5−Cl−PYR1]、[6733:3−Me−4−CN−5−Cl−PYR1]、[6734:3−Me−4−c−Pr−5−Cl−PYR1]、[6735:3−Me−4−CHF2−5−Cl−PYR1]、[6736:3−Me−4−CF3−5−Cl−PYR1]、[6737:3−Me−5−Br−PYR1]、[6738:3−Me−4−F−5−Br−PYR1]、[6739:3−Me−4−Cl−5−Br−PYR1]、[6740:3−Me−4−Br−5−Br−PYR1]、[6741:3−Me−4−Me−5−Br−PYR1]、[6742:3−Me−4−Et−5−Br−PYR1]、[6743:3−Me−4−OMe−5−Br−PYR1]、[6744:3−Me−4−OEt−5−Br−PYR1]、[6745:3−Me−4−CN−5−Br−PYR1]、[6746:3−Me−4−c−Pr−5−Br−PYR1]、[6747:3−Me−4−CHF2−5−Br−PYR1]、[6748:3−Me−4−CF3−5−Br−PYR1]、[6749:3−Me−5−Me−PYR1]、[6750:3−Me−4−F−5−Me−PYR1]、[6751:3−Me−4−Cl−5−Me−PYR1]、[6752:3−Me−4−Br−5−Me−PYR1]、[6753:3−Me−4−Me−5−Me−PYR1]、[6754:3−Me−4−Et−5−Me−PYR1]、[6755:3−Me−4−OMe−5−Me−PYR1]、[6756:3−Me−4−OEt−5−Me−PYR1]、[6757:3−Me−4−CN−5−Me−PYR1]、[6758:3−Me−4−c−Pr−5−Me−PYR1]、[6759:3−Me−4−CHF2−5−Me−PYR1]、[6760:3−Me−4−CF3−5−Me−PYR1]、[6761:3−Me−5−Et−PYR1]、[6762:3−Me−4−F−5−Et−PYR1]、[6763:3−Me−4−Cl−5−Et−PYR1]、[6764:3−Me−4−Br−5−Et−PYR1]、[6765:3−Me−4−Me−5−Et−PYR1]、[6766:3−Me−4−Et−5−Et−PYR1]、[6767:3−Me−4−OMe−5−Et−PYR1]、[6768:3−Me−4−OEt−5−Et−PYR1]、[6769:3−Me−4−CN−5−Et−PYR1]、[6770:3−Me−4−c−Pr−5−Et−PYR1]、[6771:3−Me−4−CHF2−5−Et−PYR1]、[6772:3−Me−4−CF3−5−Et−PYR1]、[6773:3−Me−5−OMe−PYR1]、[6774:3−Me−4−F−5−OMe−PYR1]、[6775:3−Me−4−Cl−5−OMe−PYR1]、[6776:3−Me−4−Br−5−OMe−PYR1]、[6777:3−Me−4−Me−5−OMe−PYR1]、[6778:3−Me−4−Et−5−OMe−PYR1]、[6779:3−Me−4−OMe−5−OMe−PYR1]、[6780:3−Me−4−OEt−5−OMe−PYR1]、[6781:3−Me−4−CN−5−OMe−PYR1]、[6782:3−Me−4−c−Pr−5−OMe−PYR1]、[6783:3−Me−4−CHF2−5−OMe−PYR1]、[6784:3−Me−4−CF3−5−OMe−PYR1]、[6785:3−Me−5−OEt−PYR1]、[6786:3−Me−4−F−5−OEt−PYR1]、[6787:3−Me−4−Cl−5−OEt−PYR1]、[6788:3−Me−4−Br−5−OEt−PYR1]、[6789:3−Me−4−Me−5−OEt−PYR1]、[6790:3−Me−4−Et−5−OEt−PYR1]、[6791:3−Me−4−OMe−5−OEt−PYR1]、[6792:3−Me−4−OEt−5−OEt−PYR1]、[6793:3−Me−4−CN−5−OEt−PYR1]、[6794:3−Me−4−c−Pr−5−OEt−PYR1]、[6795:3−Me−4−CHF2−5−OEt−PYR1]、[6796:3−Me−4−CF3−5−OEt−PYR1]、[6797:3−Me−5−CN−PYR1]、[6798:3−Me−4−F−5−CN−PYR1]、[6799:3−Me−4−Cl−5−CN−PYR1]、[6800:3−Me−4−Br−5−CN−PYR1]、 [6701: 3-Me-PYR1], [6702: 3-Me-4-F-PYR1], [6703: 3-Me-4-Cl-PYR1], [6704: 3-Me-4-Br-PYR1] ], [6705: 3-Me-4-Me-PYR1], [6706: 3-Me-4-Et-PYR1], [6707: 3-Me-4-OMe-PYR1], [6708: 3-Me. -4-OEt-PYR1], [6709: 3-Me-4-CN-PYR1], [6710: 3-Me-4-c-Pr-PYR1], [6711: 3-Me-4-CHF2-PYR1] ], [6712: 3-Me-4-CF3-PYR1], [6713: 3-Me-5-F-PYR1], [6714: 3-Me-4-F-5-F-PYR1], [6715]. : 3-Me-4-Cl-5-F-PY 1], [6716: 3-Me-4-Br-5-F-PYR1], [6717: 3-Me-4-Me-5-F-PYR1], [6718: 3-Me-4-Et- 5-F-PYR1], [6719: 3-Me-4-OMe-5-F-PYR1], [6720: 3-Me-4-OEt-5-F-PYR1], [6721: 3-Me- 4-CN-5-F-PYR1], [6722: 3-Me-4-c-Pr-5-F-PYR1], [6723: 3-Me-4-CHF2-5-F-PYR1], [ 6724: 3-Me-4-CF3-5-F-PYR1], [6725: 3-Me-5-Cl-PYR1], [6726: 3-Me-4-F-5-Cl-PYR1], [ 6727: 3-Me-4-Cl-5-Cl-PYR1], [6728: 3-Me-4- r-5-Cl-PYR1], [6729: 3-Me-4-Me-5-Cl-PYR1], [6730: 3-Me-4-Et-5-Cl-PYR1], [6731: 3- Me-4-OMe-5-Cl-PYR1], [6732: 3-Me-4-OEt-5-Cl-PYR1], [6733: 3-Me-4-CN-5-Cl-PYR1], [ 6734: 3-Me-4-c-Pr-5-Cl-PYR1], [6735: 3-Me-4-CHF2-5-Cl-PYR1], [6736: 3-Me-4-CF3-5 Cl-PYR1], [6737: 3-Me-5-Br-PYR1], [6738: 3-Me-4-F-5-Br-PYR1], [6739: 3-Me-4-Cl-5 Br-PYR1], [6740: 3-Me-4-Br-5-Br-P YR1], [6741: 3-Me-4-Me-5-Br-PYR1], [6742: 3-Me-4-Et-5-Br-PYR1], [6743: 3-Me-4-OMe- 5-Br-PYR1], [6744: 3-Me-4-OEt-5-Br-PYR1], [6745: 3-Me-4-CN-5-Br-PYR1], [6746: 3-Me- 4-c-Pr-5-Br-PYR1], [6747: 3-Me-4-CHF2-5-Br-PYR1], [6748: 3-Me-4-CF3-5-Br-PYR1], [ 6749: 3-Me-5-Me-PYR1], [6750: 3-Me-4-F-5-Me-PYR1], [6751: 3-Me-4-Cl-5-Me-PYR1], [ 6752: 3-Me-4-Br-5-Me-PYR1], [67 3: 3-Me-4-Me-5-Me-PYR1], [6754: 3-Me-4-Et-5-Me-PYR1], [6755: 3-Me-4-OMe-5-Me- PYR1], [6756: 3-Me-4-OEt-5-Me-PYR1], [6757: 3-Me-4-CN-5-Me-PYR1], [6758: 3-Me-4-c- Pr-5-Me-PYR1], [6759: 3-Me-4-CHF2-5-Me-PYR1], [6760: 3-Me-4-CF3-5-Me-PYR1], [6761: 3- Me-5-Et-PYR1], [6762: 3-Me-4-F-5-Et-PYR1], [6763: 3-Me-4-Cl-5-Et-PYR1], [6764: 3- Me-4-Br-5-Et-PYR1], [6765: 3-Me- -Me-5-Et-PYR1], [6766: 3-Me-4-Et-5-Et-PYR1], [6767: 3-Me-4-OMe-5-Et-PYR1], [6768: 3. -Me-4-OEt-5-Et-PYR1], [6769: 3-Me-4-CN-5-Et-PYR1], [6770: 3-Me-4-c-Pr-5-Et-PYR1] ], [6711: 3-Me-4-CHF2-5-Et-PYR1], [6772: 3-Me-4-CF3-5-Et-PYR1], [6773: 3-Me-5-OMe-PYR1] ], [6774: 3-Me-4-F-5-OMe-PYR1], [6775: 3-Me-4-Cl-5-OMe-PYR1], [6776: 3-Me-4-Br-5]. -OMe-PYR1], [6777: 3-Me-4-Me- 5-OMe-PYR1], [6778: 3-Me-4-Et-5-OMe-PYR1], [6779: 3-Me-4-OMe-5-OMe-PYR1], [6780: 3-Me- 4-OEt-5-OMe-PYR1], [6781: 3-Me-4-CN-5-OMe-PYR1], [6782: 3-Me-4-c-Pr-5-OMe-PYR1], [ 6783: 3-Me-4-CHF2-5-OMe-PYR1], [6784: 3-Me-4-CF3-5-OMe-PYR1], [6785: 3-Me-5-OEt-PYR1], [ 6786: 3-Me-4-F-5-OEt-PYR1], [6787: 3-Me-4-Cl-5-OEt-PYR1], [6788: 3-Me-4-Br-5-OEt- PYR1], [6789: 3-Me-4 Me-5-OEt-PYR1], [6790: 3-Me-4-Et-5-OEt-PYR1], [6791: 3-Me-4-OMe-5-OEt-PYR1], [6792: 3- Me-4-OEt-5-OEt-PYR1], [6793: 3-Me-4-CN-5-OEt-PYR1], [6794: 3-Me-4-c-Pr-5-OEt-PYR1] [6795: 3-Me-4-CHF2-5-OEt-PYR1], [6796: 3-Me-4-CF3-5-OEt-PYR1], [6797: 3-Me-5-CN-PYR1] [6798: 3-Me-4-F-5-CN-PYR1], [6799: 3-Me-4-Cl-5-CN-PYR1], [6800: 3-Me-4-Br-5-5]. CN-PYR1],
[6801:3−Me−4−Me−5−CN−PYR1]、[6802:3−Me−4−Et−5−CN−PYR1]、[6803:3−Me−4−OMe−5−CN−PYR1]、[6804:3−Me−4−OEt−5−CN−PYR1]、[6805:3−Me−4−CN−5−CN−PYR1]、[6806:3−Me−4−c−Pr−5−CN−PYR1]、[6807:3−Me−4−CHF2−5−CN−PYR1]、[6808:3−Me−4−CF3−5−CN−PYR1]、[6809:3−Me−5−c−Pr−PYR1]、[6810:3−Me−4−F−5−c−Pr−PYR1]、[6811:3−Me−4−Cl−5−c−Pr−PYR1]、[6812:3−Me−4−Br−5−c−Pr−PYR1]、[6813:3−Me−4−Me−5−c−Pr−PYR1]、[6814:3−Me−4−Et−5−c−Pr−PYR1]、[6815:3−Me−4−OMe−5−c−Pr−PYR1]、[6816:3−Me−4−OEt−5−c−Pr−PYR1]、[6817:3−Me−4−CN−5−c−Pr−PYR1]、[6818:3−Me−4−c−Pr−5−c−Pr−PYR1]、[6819:3−Me−4−CHF2−5−c−Pr−PYR1]、[6820:3−Me−4−CF3−5−c−Pr−PYR1]、[6821:3−Me−5−CHF2−PYR1]、[6822:3−Me−4−F−5−CHF2−PYR1]、[6823:3−Me−4−Cl−5−CHF2−PYR1]、[6824:3−Me−4−Br−5−CHF2−PYR1]、[6825:3−Me−4−Me−5−CHF2−PYR1]、[6826:3−Me−4−Et−5−CHF2−PYR1]、[6827:3−Me−4−OMe−5−CHF2−PYR1]、[6828:3−Me−4−OEt−5−CHF2−PYR1]、[6829:3−Me−4−CN−5−CHF2−PYR1]、[6830:3−Me−4−c−Pr−5−CHF2−PYR1]、[6831:3−Me−4−CHF2−5−CHF2−PYR1]、[6832:3−Me−4−CF3−5−CHF2−PYR1]、[6833:3−Me−5−CF3−PYR1]、[6834:3−Me−4−F−5−CF3−PYR1]、[6835:3−Me−4−Cl−5−CF3−PYR1]、[6836:3−Me−4−Br−5−CF3−PYR1]、[6837:3−Me−4−Me−5−CF3−PYR1]、[6838:3−Me−4−Et−5−CF3−PYR1]、[6839:3−Me−4−OMe−5−CF3−PYR1]、[6840:3−Me−4−OEt−5−CF3−PYR1]、[6841:3−Me−4−CN−5−CF3−PYR1]、[6842:3−Me−4−c−Pr−5−CF3−PYR1]、[6843:3−Me−4−CHF2−5−CF3−PYR1]、[6844:3−Me−4−CF3−5−CF3−PYR1]、[6845:3−Et−PYR1]、[6846:3−Et−4−F−PYR1]、[6847:3−Et−4−Cl−PYR1]、[6848:3−Et−4−Br−PYR1]、[6849:3−Et−4−Me−PYR1]、[6850:3−Et−4−Et−PYR1]、[6851:3−Et−4−OMe−PYR1]、[6852:3−Et−4−OEt−PYR1]、[6853:3−Et−4−CN−PYR1]、[6854:3−Et−4−c−Pr−PYR1]、[6855:3−Et−4−CHF2−PYR1]、[6856:3−Et−4−CF3−PYR1]、[6857:3−Et−5−F−PYR1]、[6858:3−Et−4−F−5−F−PYR1]、[6859:3−Et−4−Cl−5−F−PYR1]、[6860:3−Et−4−Br−5−F−PYR1]、[6861:3−Et−4−Me−5−F−PYR1]、[6862:3−Et−4−Et−5−F−PYR1]、[6863:3−Et−4−OMe−5−F−PYR1]、[6864:3−Et−4−OEt−5−F−PYR1]、[6865:3−Et−4−CN−5−F−PYR1]、[6866:3−Et−4−c−Pr−5−F−PYR1]、[6867:3−Et−4−CHF2−5−F−PYR1]、[6868:3−Et−4−CF3−5−F−PYR1]、[6869:3−Et−5−Cl−PYR1]、[6870:3−Et−4−F−5−Cl−PYR1]、[6871:3−Et−4−Cl−5−Cl−PYR1]、[6872:3−Et−4−Br−5−Cl−PYR1]、[6873:3−Et−4−Me−5−Cl−PYR1]、[6874:3−Et−4−Et−5−Cl−PYR1]、[6875:3−Et−4−OMe−5−Cl−PYR1]、[6876:3−Et−4−OEt−5−Cl−PYR1]、[6877:3−Et−4−CN−5−Cl−PYR1]、[6878:3−Et−4−c−Pr−5−Cl−PYR1]、[6879:3−Et−4−CHF2−5−Cl−PYR1]、[6880:3−Et−4−CF3−5−Cl−PYR1]、[6881:3−Et−5−Br−PYR1]、[6882:3−Et−4−F−5−Br−PYR1]、[6883:3−Et−4−Cl−5−Br−PYR1]、[6884:3−Et−4−Br−5−Br−PYR1]、[6885:3−Et−4−Me−5−Br−PYR1]、[6886:3−Et−4−Et−5−Br−PYR1]、[6887:3−Et−4−OMe−5−Br−PYR1]、[6888:3−Et−4−OEt−5−Br−PYR1]、[6889:3−Et−4−CN−5−Br−PYR1]、[6890:3−Et−4−c−Pr−5−Br−PYR1]、[6891:3−Et−4−CHF2−5−Br−PYR1]、[6892:3−Et−4−CF3−5−Br−PYR1]、[6893:3−Et−5−Me−PYR1]、[6894:3−Et−4−F−5−Me−PYR1]、[6895:3−Et−4−Cl−5−Me−PYR1]、[6896:3−Et−4−Br−5−Me−PYR1]、[6897:3−Et−4−Me−5−Me−PYR1]、[6898:3−Et−4−Et−5−Me−PYR1]、[6899:3−Et−4−OMe−5−Me−PYR1]、[6900:3−Et−4−OEt−5−Me−PYR1]、 [6801: 3-Me-4-Me-5-CN-PYR1], [6802: 3-Me-4-Et-5-CN-PYR1], [6803: 3-Me-4-OMe-5-CN -PYR1], [6804: 3-Me-4-OEt-5-CN-PYR1], [6805: 3-Me-4-CN-5-CN-PYR1], [6806: 3-Me-4-c -Pr-5-CN-PYR1], [6807: 3-Me-4-CHF2-5-CN-PYR1], [6808: 3-Me-4-CF3-5-CN-PYR1], [6809: 3 -Me-5-c-Pr-PYR1], [6810: 3-Me-4-F-5-c-Pr-PYR1], [6811: 3-Me-4-Cl-5-c-Pr-PYR1] ], [6812: 3-Me-4-Br-5-c-Pr-PYR1], 6813: 3-Me-4-Me-5-c-Pr-PYR1], [6814: 3-Me-4-Et-5-c-Pr-PYR1], [6815: 3-Me-4-OMe- 5-c-Pr-PYR1], [6816: 3-Me-4-OEt-5-c-Pr-PYR1], [6817: 3-Me-4-CN-5-c-Pr-PYR1], [ 6818: 3-Me-4-c-Pr-5-c-Pr-PYR1], [6819: 3-Me-4-CHF2-5-c-Pr-PYR1], [6820: 3-Me-4- CF3-5-c-Pr-PYR1], [6821: 3-Me-5-CHF2-PYR1], [6822: 3-Me-4-F-5-CHF2-PYR1], [6823: 3-Me- 4-Cl-5-CHF2-PYR1], [6824: 3-Me-4- r-5-CHF2-PYR1], [6825: 3-Me-4-Me-5-CHF2-PYR1], [6826: 3-Me-4-Et-5-CHF2-PYR1], [6827: 3- Me-4-OMe-5-CHF2-PYR1], [6828: 3-Me-4-OEt-5-CHF2-PYR1], [6829: 3-Me-4-CN-5-CHF2-PYR1], [ 6830: 3-Me-4-c-Pr-5-CHF2-PYR1], [6831: 3-Me-4-CHF2-5-CHF2-PYR1], [6832: 3-Me-4-CF3-5 CHF2-PYR1], [6833: 3-Me-5-CF3-PYR1], [6834: 3-Me-4-F-5-CF3-PYR1], [6835: 3-Me-4-Cl-5] CF3-PYR1], [ 6836: 3-Me-4-Br-5-CF3-PYR1], [6837: 3-Me-4-Me-5-CF3-PYR1], [6838: 3-Me-4-Et-5-CF3- PYR1], [6839: 3-Me-4-OMe-5-CF3-PYR1], [6840: 3-Me-4-OEt-5-CF3-PYR1], [6841: 3-Me-4-CN- 5-CF3-PYR1], [6842: 3-Me-4-c-Pr-5-CF3-PYR1], [6843: 3-Me-4-CHF2-5-CF3-PYR1], [6844: 3- Me-4-CF3-5-CF3-PYR1], [6845: 3-Et-PYR1], [6846: 3-Et-4-F-PYR1], [6847: 3-Et-4-Cl-PYR1] [6848: 3-Et-4-Br PYR1], [6849: 3-Et-4-Me-PYR1], [6850: 3-Et-4-Et-PYR1], [6851: 3-Et-4-OMe-PYR1], [6852: 3- Et-4-OEt-PYR1], [6853: 3-Et-4-CN-PYR1], [6854: 3-Et-4-c-Pr-PYR1], [6855: 3-Et-4-CHF2- PYR1], [6856: 3-Et-4-CF3-PYR1], [6857: 3-Et-5-F-PYR1], [6858: 3-Et-4-F-5-F-PYR1], [ 6859: 3-Et-4-Cl-5-F-PYR1], [6860: 3-Et-4-Br-5-F-PYR1], [6861: 3-Et-4-Me-5-F- PYR1], [6862: 3-Et-4-Et-5-F PYR1], [6863: 3-Et-4-OMe-5-F-PYR1], [6864: 3-Et-4-OEt-5-F-PYR1], [6865: 3-Et-4-CN- 5-F-PYR1], [6866: 3-Et-4-c-Pr-5-F-PYR1], [6867: 3-Et-4-CHF2-5-F-PYR1], [6868: 3- Et-4-CF3-5-F-PYR1], [6869: 3-Et-5-Cl-PYR1], [6870: 3-Et-4-F-5-Cl-PYR1], [6871: 3- Et-4-Cl-5-Cl-PYR1], [6872: 3-Et-4-Br-5-Cl-PYR1], [6873: 3-Et-4-Me-5-Cl-PYR1], [ 6874: 3-Et-4-Et-5-Cl-PYR1], [6875: 3- Et-4-OMe-5-Cl-PYR1], [6876: 3-Et-4-OEt-5-Cl-PYR1], [6877: 3-Et-4-CN-5-Cl-PYR1], [ 6878: 3-Et-4-c-Pr-5-Cl-PYR1], [6879: 3-Et-4-CHF2-5-Cl-PYR1], [6880: 3-Et-4-CF3-5 Cl-PYR1], [6881: 3-Et-5-Br-PYR1], [6882: 3-Et-4-F-5-Br-PYR1], [6883: 3-Et-4-Cl-5-5 Br-PYR1], [6884: 3-Et-4-Br-5-Br-PYR1], [6885: 3-Et-4-Me-5-Br-PYR1], [6886: 3-Et-4- Et-5-Br-PYR1], [6887: 3-Et-4-OMe 5-Br-PYR1], [6888: 3-Et-4-OEt-5-Br-PYR1], [6889: 3-Et-4-CN-5-Br-PYR1], [6890: 3-Et- 4-c-Pr-5-Br-PYR1], [6891: 3-Et-4-CHF2-5-Br-PYR1], [6882: 3-Et-4-CF3-5-Br-PYR1], [ 6893: 3-Et-5-Me-PYR1], [6894: 3-Et-4-F-5-Me-PYR1], [6895: 3-Et-4-Cl-5-Me-PYR1], [ 6896: 3-Et-4-Br-5-Me-PYR1], [6897: 3-Et-4-Me-5-Me-PYR1], [6898: 3-Et-4-Et-5-Me- PYR1], [6899: 3-Et-4-OMe-5-Me-PY 1], [6900: 3-Et-4-OEt-5-Me-PYR1],
[6901:3−Et−4−CN−5−Me−PYR1]、[6902:3−Et−4−c−Pr−5−Me−PYR1]、[6903:3−Et−4−CHF2−5−Me−PYR1]、[6904:3−Et−4−CF3−5−Me−PYR1]、[6905:3−Et−5−Et−PYR1]、[6906:3−Et−4−F−5−Et−PYR1]、[6907:3−Et−4−Cl−5−Et−PYR1]、[6908:3−Et−4−Br−5−Et−PYR1]、[6909:3−Et−4−Me−5−Et−PYR1]、[6910:3−Et−4−Et−5−Et−PYR1]、[6911:3−Et−4−OMe−5−Et−PYR1]、[6912:3−Et−4−OEt−5−Et−PYR1]、[6913:3−Et−4−CN−5−Et−PYR1]、[6914:3−Et−4−c−Pr−5−Et−PYR1]、[6915:3−Et−4−CHF2−5−Et−PYR1]、[6916:3−Et−4−CF3−5−Et−PYR1]、[6917:3−Et−5−OMe−PYR1]、[6918:3−Et−4−F−5−OMe−PYR1]、[6919:3−Et−4−Cl−5−OMe−PYR1]、[6920:3−Et−4−Br−5−OMe−PYR1]、[6921:3−Et−4−Me−5−OMe−PYR1]、[6922:3−Et−4−Et−5−OMe−PYR1]、[6923:3−Et−4−OMe−5−OMe−PYR1]、[6924:3−Et−4−OEt−5−OMe−PYR1]、[6925:3−Et−4−CN−5−OMe−PYR1]、[6926:3−Et−4−c−Pr−5−OMe−PYR1]、[6927:3−Et−4−CHF2−5−OMe−PYR1]、[6928:3−Et−4−CF3−5−OMe−PYR1]、[6929:3−Et−5−OEt−PYR1]、[6930:3−Et−4−F−5−OEt−PYR1]、[6931:3−Et−4−Cl−5−OEt−PYR1]、[6932:3−Et−4−Br−5−OEt−PYR1]、[6933:3−Et−4−Me−5−OEt−PYR1]、[6934:3−Et−4−Et−5−OEt−PYR1]、[6935:3−Et−4−OMe−5−OEt−PYR1]、[6936:3−Et−4−OEt−5−OEt−PYR1]、[6937:3−Et−4−CN−5−OEt−PYR1]、[6938:3−Et−4−c−Pr−5−OEt−PYR1]、[6939:3−Et−4−CHF2−5−OEt−PYR1]、[6940:3−Et−4−CF3−5−OEt−PYR1]、[6941:3−Et−5−CN−PYR1]、[6942:3−Et−4−F−5−CN−PYR1]、[6943:3−Et−4−Cl−5−CN−PYR1]、[6944:3−Et−4−Br−5−CN−PYR1]、[6945:3−Et−4−Me−5−CN−PYR1]、[6946:3−Et−4−Et−5−CN−PYR1]、[6947:3−Et−4−OMe−5−CN−PYR1]、[6948:3−Et−4−OEt−5−CN−PYR1]、[6949:3−Et−4−CN−5−CN−PYR1]、[6950:3−Et−4−c−Pr−5−CN−PYR1]、[6951:3−Et−4−CHF2−5−CN−PYR1]、[6952:3−Et−4−CF3−5−CN−PYR1]、[6953:3−Et−5−c−Pr−PYR1]、[6954:3−Et−4−F−5−c−Pr−PYR1]、[6955:3−Et−4−Cl−5−c−Pr−PYR1]、[6956:3−Et−4−Br−5−c−Pr−PYR1]、[6957:3−Et−4−Me−5−c−Pr−PYR1]、[6958:3−Et−4−Et−5−c−Pr−PYR1]、[6959:3−Et−4−OMe−5−c−Pr−PYR1]、[6960:3−Et−4−OEt−5−c−Pr−PYR1]、[6961:3−Et−4−CN−5−c−Pr−PYR1]、[6962:3−Et−4−c−Pr−5−c−Pr−PYR1]、[6963:3−Et−4−CHF2−5−c−Pr−PYR1]、[6964:3−Et−4−CF3−5−c−Pr−PYR1]、[6965:3−Et−5−CHF2−PYR1]、[6966:3−Et−4−F−5−CHF2−PYR1]、[6967:3−Et−4−Cl−5−CHF2−PYR1]、[6968:3−Et−4−Br−5−CHF2−PYR1]、[6969:3−Et−4−Me−5−CHF2−PYR1]、[6970:3−Et−4−Et−5−CHF2−PYR1]、[6971:3−Et−4−OMe−5−CHF2−PYR1]、[6972:3−Et−4−OEt−5−CHF2−PYR1]、[6973:3−Et−4−CN−5−CHF2−PYR1]、[6974:3−Et−4−c−Pr−5−CHF2−PYR1]、[6975:3−Et−4−CHF2−5−CHF2−PYR1]、[6976:3−Et−4−CF3−5−CHF2−PYR1]、[6977:3−Et−5−CF3−PYR1]、[6978:3−Et−4−F−5−CF3−PYR1]、[6979:3−Et−4−Cl−5−CF3−PYR1]、[6980:3−Et−4−Br−5−CF3−PYR1]、[6981:3−Et−4−Me−5−CF3−PYR1]、[6982:3−Et−4−Et−5−CF3−PYR1]、[6983:3−Et−4−OMe−5−CF3−PYR1]、[6984:3−Et−4−OEt−5−CF3−PYR1]、[6985:3−Et−4−CN−5−CF3−PYR1]、[6986:3−Et−4−c−Pr−5−CF3−PYR1]、[6987:3−Et−4−CHF2−5−CF3−PYR1]、[6988:3−Et−4−CF3−5−CF3−PYR1]、[6989:5−Me−PYR1]、[6990:3−F−5−Me−PYR1]、[6991:3−Cl−5−Me−PYR1]、[6992:3−Br−5−Me−PYR1]、[6993:3−OMe−5−Me−PYR1]、[6994:3−OEt−5−Me−PYR1]、[6995:3−CN−5−Me−PYR1]、[6996:3−c−Pr−5−Me−PYR1]、[6997:3−CHF2−5−Me−PYR1]、[6998:3−CF3−5−Me−PYR1]、[6999:4−F−5−Me−PYR1]、[7000:3−F−4−F−5−Me−PYR1]、 [6901: 3-Et-4-CN-5-Me-PYR1], [6902: 3-Et-4-c-Pr-5-Me-PYR1], [6903: 3-Et-4-CHF2-5 -Me-PYR1], [6904: 3-Et-4-CF3-5-Me-PYR1], [6905: 3-Et-5-Et-PYR1], [6906: 3-Et-4-F-5 -Et-PYR1], [6907: 3-Et-4-Cl-5-Et-PYR1], [6908: 3-Et-4-Br-5-Et-PYR1], [6909: 3-Et-4 -Me-5-Et-PYR1], [6910: 3-Et-4-Et-5-Et-PYR1], [6911: 3-Et-4-OMe-5-Et-PYR1], [6912: 3 -Et-4-OEt-5-Et-PYR1], [6913: 3- t-4-CN-5-Et-PYR1], [6914: 3-Et-4-c-Pr-5-Et-PYR1], [6915: 3-Et-4-CHF2-5-Et-PYR1] [6916: 3-Et-4-CF3-5-Et-PYR1], [6917: 3-Et-5-OMe-PYR1], [6918: 3-Et-4-F-5-OMe-PYR1] [6919: 3-Et-4-Cl-5-OMe-PYR1], [6920: 3-Et-4-Br-5-OMe-PYR1], [6921: 3-Et-4-Me-5- OMe-PYR1], [6922: 3-Et-4-Et-5-OMe-PYR1], [6923: 3-Et-4-OMe-5-OMe-PYR1], [6924: 3-Et-4- OEt-5-OMe-PYR1], [6925: 3- t-4-CN-5-OMe-PYR1], [6926: 3-Et-4-c-Pr-5-OMe-PYR1], [6927: 3-Et-4-CHF2-5-OMe-PYR1] [6928: 3-Et-4-CF3-5-OMe-PYR1], [6929: 3-Et-5-OEt-PYR1], [6930: 3-Et-4-F-5-OEt-PYR1] [6931: 3-Et-4-Cl-5-OEt-PYR1], [6932: 3-Et-4-Br-5-OEt-PYR1], [6933: 3-Et-4-Me-5 OEt-PYR1], [6934: 3-Et-4-Et-5-OEt-PYR1], [6935: 3-Et-4-OMe-5-OEt-PYR1], [6936: 3-Et-4- OEt-5-OEt-PYR1], [6937 : 3-Et-4-CN-5-OEt-PYR1], [6938: 3-Et-4-c-Pr-5-OEt-PYR1], [6939: 3-Et-4-CHF2-5-OEt -PYR1], [6940: 3-Et-4-CF3-5-OEt-PYR1], [6941: 3-Et-5-CN-PYR1], [6942: 3-Et-4-F-5-CN -PYR1], [6943: 3-Et-4-Cl-5-CN-PYR1], [6944: 3-Et-4-Br-5-CN-PYR1], [6945: 3-Et-4-Me. -5-CN-PYR1], [6946: 3-Et-4-Et-5-CN-PYR1], [6947: 3-Et-4-OMe-5-CN-PYR1], [6948: 3-Et -4-OEt-5-CN-PYR1], [6949: 3-E -4-CN-5-CN-PYR1], [6950: 3-Et-4-c-Pr-5-CN-PYR1], [6951: 3-Et-4-CHF2-5-CN-PYR1], [6952: 3-Et-4-CF3-5-CN-PYR1], [6953: 3-Et-5-c-Pr-PYR1], [6954: 3-Et-4-F-5-c-Pr -PYR1], [6955: 3-Et-4-Cl-5-c-Pr-PYR1], [6956: 3-Et-4-Br-5-c-Pr-PYR1], [6957: 3-Et -4-Me-5-c-Pr-PYR1], [6958: 3-Et-4-Et-5-c-Pr-PYR1], [6959: 3-Et-4-OMe-5-c-Pr -PYR1], [6960: 3-Et-4-OEt-5-c-Pr-PYR1], [ 961: 3-Et-4-CN-5-c-Pr-PYR1], [6962: 3-Et-4-c-Pr-5-c-Pr-PYR1], [6963: 3-Et-4- CHF2-5-c-Pr-PYR1], [6964: 3-Et-4-CF3-5-c-Pr-PYR1], [6965: 3-Et-5-CHF2-PYR1], [6966: 3- Et-4-F-5-CHF2-PYR1], [6967: 3-Et-4-Cl-5-CHF2-PYR1], [6968: 3-Et-4-Br-5-CHF2-PYR1], [ 6969: 3-Et-4-Me-5-CHF2-PYR1], [6970: 3-Et-4-Et-5-CHF2-PYR1], [6791: 3-Et-4-OMe-5-CHF2- PYR1], [6792: 3-Et-4-OEt -5-CHF2-PYR1], [6793: 3-Et-4-CN-5-CHF2-PYR1], [6974: 3-Et-4-c-Pr-5-CHF2-PYR1], [6975: 3 -Et-4-CHF2-5-CHF2-PYR1], [6976: 3-Et-4-CF3-5-CHF2-PYR1], [6977: 3-Et-5-CF3-PYR1], [6978: 3 -Et-4-F-5-CF3-PYR1], [6979: 3-Et-4-Cl-5-CF3-PYR1], [6980: 3-Et-4-Br-5-CF3-PYR1], [6981: 3-Et-4-Me-5-CF3-PYR1], [6982: 3-Et-4-Et-5-CF3-PYR1], [6983: 3-Et-4-OMe-5-CF3 -PYR1], [6984: 3 Et-4-OEt-5-CF3-PYR1], [6985: 3-Et-4-CN-5-CF3-PYR1], [6986: 3-Et-4-c-Pr-5-CF3-PYR1] [6987: 3-Et-4-CHF2-5-CF3-PYR1], [6988: 3-Et-4-CF3-5-CF3-PYR1], [6989: 5-Me-PYR1], [6990: 3-F-5-Me-PYR1], [6991: 3-Cl-5-Me-PYR1], [6992: 3-Br-5-Me-PYR1], [6993: 3-OMe-5-Me- PYR1], [6994: 3-OEt-5-Me-PYR1], [6995: 3-CN-5-Me-PYR1], [6996: 3-c-Pr-5-Me-PYR1], [6997: 3-CHF2-5-Me-PY 1], [6998: 3-CF3-5-Me-PYR1], [6999: 4-F-5-Me-PYR1], [7000: 3-F-4-F-5-Me-PYR1],
[7001:3−Cl−4−F−5−Me−PYR1]、[7002:3−Br−4−F−5−Me−PYR1]、[7003:3−OMe−4−F−5−Me−PYR1]、[7004:3−OEt−4−F−5−Me−PYR1]、[7005:3−CN−4−F−5−Me−PYR1]、[7006:3−c−Pr−4−F−5−Me−PYR1]、[7007:3−CHF2−4−F−5−Me−PYR1]、[7008:3−CF3−4−F−5−Me−PYR1]、[7009:4−Cl−5−Me−PYR1]、[7010:3−F−4−Cl−5−Me−PYR1]、[7011:3−Cl−4−Cl−5−Me−PYR1]、[7012:3−Br−4−Cl−5−Me−PYR1]、[7013:3−OMe−4−Cl−5−Me−PYR1]、[7014:3−OEt−4−Cl−5−Me−PYR1]、[7015:3−CN−4−Cl−5−Me−PYR1]、[7016:3−c−Pr−4−Cl−5−Me−PYR1]、[7017:3−CHF2−4−Cl−5−Me−PYR1]、[7018:3−CF3−4−Cl−5−Me−PYR1]、[7019:4−Br−5−Me−PYR1]、[7020:3−F−4−Br−5−Me−PYR1]、[7021:3−Cl−4−Br−5−Me−PYR1]、[7022:3−Br−4−Br−5−Me−PYR1]、[7023:3−OMe−4−Br−5−Me−PYR1]、[7024:3−OEt−4−Br−5−Me−PYR1]、[7025:3−CN−4−Br−5−Me−PYR1]、[7026:3−c−Pr−4−Br−5−Me−PYR1]、[7027:3−CHF2−4−Br−5−Me−PYR1]、[7028:3−CF3−4−Br−5−Me−PYR1]、[7029:4−Me−5−Me−PYR1]、[7030:3−F−4−Me−5−Me−PYR1]、[7031:3−Cl−4−Me−5−Me−PYR1]、[7032:3−Br−4−Me−5−Me−PYR1]、[7033:3−OMe−4−Me−5−Me−PYR1]、[7034:3−OEt−4−Me−5−Me−PYR1]、[7035:3−CN−4−Me−5−Me−PYR1]、[7036:3−c−Pr−4−Me−5−Me−PYR1]、[7037:3−CHF2−4−Me−5−Me−PYR1]、[7038:3−CF3−4−Me−5−Me−PYR1]、[7039:4−Et−5−Me−PYR1]、[7040:3−F−4−Et−5−Me−PYR1]、[7041:3−Cl−4−Et−5−Me−PYR1]、[7042:3−Br−4−Et−5−Me−PYR1]、[7043:3−OMe−4−Et−5−Me−PYR1]、[7044:3−OEt−4−Et−5−Me−PYR1]、[7045:3−CN−4−Et−5−Me−PYR1]、[7046:3−c−Pr−4−Et−5−Me−PYR1]、[7047:3−CHF2−4−Et−5−Me−PYR1]、[7048:3−CF3−4−Et−5−Me−PYR1]、[7049:4−OMe−5−Me−PYR1]、[7050:3−F−4−OMe−5−Me−PYR1]、[7051:3−Cl−4−OMe−5−Me−PYR1]、[7052:3−Br−4−OMe−5−Me−PYR1]、[7053:3−OMe−4−OMe−5−Me−PYR1]、[7054:3−OEt−4−OMe−5−Me−PYR1]、[7055:3−CN−4−OMe−5−Me−PYR1]、[7056:3−c−Pr−4−OMe−5−Me−PYR1]、[7057:3−CHF2−4−OMe−5−Me−PYR1]、[7058:3−CF3−4−OMe−5−Me−PYR1]、[7059:4−OEt−5−Me−PYR1]、[7060:3−F−4−OEt−5−Me−PYR1]、[7061:3−Cl−4−OEt−5−Me−PYR1]、[7062:3−Br−4−OEt−5−Me−PYR1]、[7063:3−OMe−4−OEt−5−Me−PYR1]、[7064:3−OEt−4−OEt−5−Me−PYR1]、[7065:3−CN−4−OEt−5−Me−PYR1]、[7066:3−c−Pr−4−OEt−5−Me−PYR1]、[7067:3−CHF2−4−OEt−5−Me−PYR1]、[7068:3−CF3−4−OEt−5−Me−PYR1]、[7069:4−CN−5−Me−PYR1]、[7070:3−F−4−CN−5−Me−PYR1]、[7071:3−Cl−4−CN−5−Me−PYR1]、[7072:3−Br−4−CN−5−Me−PYR1]、[7073:3−OMe−4−CN−5−Me−PYR1]、[7074:3−OEt−4−CN−5−Me−PYR1]、[7075:3−CN−4−CN−5−Me−PYR1]、[7076:3−c−Pr−4−CN−5−Me−PYR1]、[7077:3−CHF2−4−CN−5−Me−PYR1]、[7078:3−CF3−4−CN−5−Me−PYR1]、[7079:4−c−Pr−5−Me−PYR1]、[7080:3−F−4−c−Pr−5−Me−PYR1]、[7081:3−Cl−4−c−Pr−5−Me−PYR1]、[7082:3−Br−4−c−Pr−5−Me−PYR1]、[7083:3−OMe−4−c−Pr−5−Me−PYR1]、[7084:3−OEt−4−c−Pr−5−Me−PYR1]、[7085:3−CN−4−c−Pr−5−Me−PYR1]、[7086:3−c−Pr−4−c−Pr−5−Me−PYR1]、[7087:3−CHF2−4−c−Pr−5−Me−PYR1]、[7088:3−CF3−4−c−Pr−5−Me−PYR1]、[7089:4−CHF2−5−Me−PYR1]、[7090:3−F−4−CHF2−5−Me−PYR1]、[7091:3−Cl−4−CHF2−5−Me−PYR1]、[7092:3−Br−4−CHF2−5−Me−PYR1]、[7093:3−OMe−4−CHF2−5−Me−PYR1]、[7094:3−OEt−4−CHF2−5−Me−PYR1]、[7095:3−CN−4−CHF2−5−Me−PYR1]、[7096:3−c−Pr−4−CHF2−5−Me−PYR1]、[7097:3−CHF2−4−CHF2−5−Me−PYR1]、[7098:3−CF3−4−CHF2−5−Me−PYR1]、[7099:4−CF3−5−Me−PYR1]、[7100:3−F−4−CF3−5−Me−PYR1]、 [7001: 3-Cl-4-F-5-Me-PYR1], [7002: 3-Br-4-F-5-Me-PYR1], [7003: 3-OMe-4-F-5-Me -PYR1], [7004: 3-OEt-4-F-5-Me-PYR1], [7005: 3-CN-4-F-5-Me-PYR1], [7006: 3-c-Pr-4 -F-5-Me-PYR1], [7007: 3-CHF2-4-F-5-Me-PYR1], [7008: 3-CF3-4-F-5-Me-PYR1], [7009: 4. -Cl-5-Me-PYR1], [7010: 3-F-4-Cl-5-Me-PYR1], [7011: 3-Cl-4-Cl-5-Me-PYR1], [7012: 3 -Br-4-Cl-5-Me-PYR1], [7013: 3-OMe-4-Cl 5-Me-PYR1], [7014: 3-OEt-4-Cl-5-Me-PYR1], [7015: 3-CN-4-Cl-5-Me-PYR1], [7016: 3-c- Pr-4-Cl-5-Me-PYR1], [7017: 3-CHF2-4-Cl-5-Me-PYR1], [7018: 3-CF3-4-Cl-5-Me-PYR1], [ 7019: 4-Br-5-Me-PYR1], [7020: 3-F-4-Br-5-Me-PYR1], [7021: 3-Cl-4-Br-5-Me-PYR1], [ 7022: 3-Br-4-Br-5-Me-PYR1], [7023: 3-OMe-4-Br-5-Me-PYR1], [7024: 3-OEt-4-Br-5-Me- PYR1], [7025: 3-CN-4-Br-5-Me-P R1], [7026: 3-c-Pr-4-Br-5-Me-PYR1], [7027: 3-CHF2-4-Br-5-Me-PYR1], [7028: 3-CF3-4- Br-5-Me-PYR1], [7029: 4-Me-5-Me-PYR1], [7030: 3-F-4-Me-5-Me-PYR1], [7031: 3-Cl-4- Me-5-Me-PYR1], [7032: 3-Br-4-Me-5-Me-PYR1], [7033: 3-OMe-4-Me-5-Me-PYR1], [7034: 3- OEt-4-Me-5-Me-PYR1], [7035: 3-CN-4-Me-5-Me-PYR1], [7036: 3-c-Pr-4-Me-5-Me-PYR1] [7037: 3-CHF2-4-Me-5-Me-PYR1], [7038: 3-CF3-4-Me-5-Me-PYR1], [7039: 4-Et-5-Me-PYR1], [7040: 3-F-4-Et-5-Me-PYR1], [7041: 3-Cl-4-Et-5-Me-PYR1], [7042: 3-Br-4-Et-5-Me-PYR1], [7043: 3-OMe-4-Et-5-Me -PYR1], [7044: 3-OEt-4-Et-5-Me-PYR1], [7045: 3-CN-4-Et-5-Me-PYR1], [7046: 3-c-Pr-4 -Et-5-Me-PYR1], [7047: 3-CHF2-4-Et-5-Me-PYR1], [7048: 3-CF3-4-Et-5-Me-PYR1], [7049: 4 -OMe-5-Me-PYR1], [7050: 3-F-4 OMe-5-Me-PYR1], [7051: 3-Cl-4-OMe-5-Me-PYR1], [7052: 3-Br-4-OMe-5-Me-PYR1], [7053: 3- OMe-4-OMe-5-Me-PYR1], [7054: 3-OEt-4-OMe-5-Me-PYR1], [7055: 3-CN-4-OMe-5-Me-PYR1], [ 7056: 3-c-Pr-4-OMe-5-Me-PYR1], [7057: 3-CHF2-4-OMe-5-Me-PYR1], [7058: 3-CF3-4-OMe-5 Me-PYR1], [7059: 4-OEt-5-Me-PYR1], [7060: 3-F-4-OEt-5-Me-PYR1], [7061: 3-Cl-4-OEt-5 Me-PYR1], [7062: 3- r-4-OEt-5-Me-PYR1], [7063: 3-OMe-4-OEt-5-Me-PYR1], [7064: 3-OEt-4-OEt-5-Me-PYR1], [ 7065: 3-CN-4-OEt-5-Me-PYR1], [7066: 3-c-Pr-4-OEt-5-Me-PYR1], [7067: 3-CHF2-4-OEt-5 Me-PYR1], [7068: 3-CF3-4-OEt-5-Me-PYR1], [7069: 4-CN-5-Me-PYR1], [7070: 3-F-4-CN-5 Me-PYR1], [7071: 3-Cl-4-CN-5-Me-PYR1], [7072: 3-Br-4-CN-5-Me-PYR1], [7073: 3-OMe-4- CN-5-Me-PYR1], [7074: 3-O Et-4-CN-5-Me-PYR1], [7075: 3-CN-4-CN-5-Me-PYR1], [7076: 3-c-Pr-4-CN-5-Me-PYR1] [7077: 3-CHF2-4-CN-5-Me-PYR1], [7078: 3-CF3-4-CN-5-Me-PYR1], [7079: 4-c-Pr-5-Me- PYR1], [7080: 3-F-4-c-Pr-5-Me-PYR1], [7081: 3-Cl-4-c-Pr-5-Me-PYR1], [7082: 3-Br- 4-c-Pr-5-Me-PYR1], [7083: 3-OMe-4-c-Pr-5-Me-PYR1], [7084: 3-OEt-4-c-Pr-5-Me- PYR1], [7085: 3-CN-4-c-Pr-5-Me-PYR1], [7 86: 3-c-Pr-4-c-Pr-5-Me-PYR1], [7087: 3-CHF2-4-c-Pr-5-Me-PYR1], [7088: 3-CF3-4- c-Pr-5-Me-PYR1], [7089: 4-CHF2-5-Me-PYR1], [7090: 3-F-4-CHF2-5-Me-PYR1], [7091: 3-Cl- 4-CHF2-5-Me-PYR1], [7092: 3-Br-4-CHF2-5-Me-PYR1], [7093: 3-OMe-4-CHF2-5-Me-PYR1], [7094: 3-OEt-4-CHF2-5-Me-PYR1], [7095: 3-CN-4-CHF2-5-Me-PYR1], [7096: 3-c-Pr-4-CHF2-5-Me- PYR1], [7097: 3-CHF2- -CHF2-5-Me-PYR1], [7098: 3-CF3-4-CHF2-5-Me-PYR1], [7099: 4-CF3-5-Me-PYR1], [7100: 3-F-4. -CF3-5-Me-PYR1],
[7101:3−Cl−4−CF3−5−Me−PYR1]、[7102:3−Br−4−CF3−5−Me−PYR1]、[7103:3−OMe−4−CF3−5−Me−PYR1]、[7104:3−OEt−4−CF3−5−Me−PYR1]、[7105:3−CN−4−CF3−5−Me−PYR1]、[7106:3−c−Pr−4−CF3−5−Me−PYR1]、[7107:3−CHF2−4−CF3−5−Me−PYR1]、[7108:3−CF3−4−CF3−5−Me−PYR1]、[7109:5−Et−PYR1]、[7110:3−F−5−Et−PYR1]、[7111:3−Cl−5−Et−PYR1]、[7112:3−Br−5−Et−PYR1]、[7113:3−OMe−5−Et−PYR1]、[7114:3−OEt−5−Et−PYR1]、[7115:3−CN−5−Et−PYR1]、[7116:3−c−Pr−5−Et−PYR1]、[7117:3−CHF2−5−Et−PYR1]、[7118:3−CF3−5−Et−PYR1]、[7119:4−F−5−Et−PYR1]、[7120:3−F−4−F−5−Et−PYR1]、[7121:3−Cl−4−F−5−Et−PYR1]、[7122:3−Br−4−F−5−Et−PYR1]、[7123:3−OMe−4−F−5−Et−PYR1]、[7124:3−OEt−4−F−5−Et−PYR1]、[7125:3−CN−4−F−5−Et−PYR1]、[7126:3−c−Pr−4−F−5−Et−PYR1]、[7127:3−CHF2−4−F−5−Et−PYR1]、[7128:3−CF3−4−F−5−Et−PYR1]、[7129:4−Cl−5−Et−PYR1]、[7130:3−F−4−Cl−5−Et−PYR1]、[7131:3−Cl−4−Cl−5−Et−PYR1]、[7132:3−Br−4−Cl−5−Et−PYR1]、[7133:3−OMe−4−Cl−5−Et−PYR1]、[7134:3−OEt−4−Cl−5−Et−PYR1]、[7135:3−CN−4−Cl−5−Et−PYR1]、[7136:3−c−Pr−4−Cl−5−Et−PYR1]、[7137:3−CHF2−4−Cl−5−Et−PYR1]、[7138:3−CF3−4−Cl−5−Et−PYR1]、[7139:4−Br−5−Et−PYR1]、[7140:3−F−4−Br−5−Et−PYR1]、[7141:3−Cl−4−Br−5−Et−PYR1]、[7142:3−Br−4−Br−5−Et−PYR1]、[7143:3−OMe−4−Br−5−Et−PYR1]、[7144:3−OEt−4−Br−5−Et−PYR1]、[7145:3−CN−4−Br−5−Et−PYR1]、[7146:3−c−Pr−4−Br−5−Et−PYR1]、[7147:3−CHF2−4−Br−5−Et−PYR1]、[7148:3−CF3−4−Br−5−Et−PYR1]、[7149:4−Me−5−Et−PYR1]、[7150:3−F−4−Me−5−Et−PYR1]、[7151:3−Cl−4−Me−5−Et−PYR1]、[7152:3−Br−4−Me−5−Et−PYR1]、[7153:3−OMe−4−Me−5−Et−PYR1]、[7154:3−OEt−4−Me−5−Et−PYR1]、[7155:3−CN−4−Me−5−Et−PYR1]、[7156:3−c−Pr−4−Me−5−Et−PYR1]、[7157:3−CHF2−4−Me−5−Et−PYR1]、[7158:3−CF3−4−Me−5−Et−PYR1]、[7159:4−Et−5−Et−PYR1]、[7160:3−F−4−Et−5−Et−PYR1]、[7161:3−Cl−4−Et−5−Et−PYR1]、[7162:3−Br−4−Et−5−Et−PYR1]、[7163:3−OMe−4−Et−5−Et−PYR1]、[7164:3−OEt−4−Et−5−Et−PYR1]、[7165:3−CN−4−Et−5−Et−PYR1]、[7166:3−c−Pr−4−Et−5−Et−PYR1]、[7167:3−CHF2−4−Et−5−Et−PYR1]、[7168:3−CF3−4−Et−5−Et−PYR1]、[7169:4−OMe−5−Et−PYR1]、[7170:3−F−4−OMe−5−Et−PYR1]、[7171:3−Cl−4−OMe−5−Et−PYR1]、[7172:3−Br−4−OMe−5−Et−PYR1]、[7173:3−OMe−4−OMe−5−Et−PYR1]、[7174:3−OEt−4−OMe−5−Et−PYR1]、[7175:3−CN−4−OMe−5−Et−PYR1]、[7176:3−c−Pr−4−OMe−5−Et−PYR1]、[7177:3−CHF2−4−OMe−5−Et−PYR1]、[7178:3−CF3−4−OMe−5−Et−PYR1]、[7179:4−OEt−5−Et−PYR1]、[7180:3−F−4−OEt−5−Et−PYR1]、[7181:3−Cl−4−OEt−5−Et−PYR1]、[7182:3−Br−4−OEt−5−Et−PYR1]、[7183:3−OMe−4−OEt−5−Et−PYR1]、[7184:3−OEt−4−OEt−5−Et−PYR1]、[7185:3−CN−4−OEt−5−Et−PYR1]、[7186:3−c−Pr−4−OEt−5−Et−PYR1]、[7187:3−CHF2−4−OEt−5−Et−PYR1]、[7188:3−CF3−4−OEt−5−Et−PYR1]、[7189:4−CN−5−Et−PYR1]、[7190:3−F−4−CN−5−Et−PYR1]、[7191:3−Cl−4−CN−5−Et−PYR1]、[7192:3−Br−4−CN−5−Et−PYR1]、[7193:3−OMe−4−CN−5−Et−PYR1]、[7194:3−OEt−4−CN−5−Et−PYR1]、[7195:3−CN−4−CN−5−Et−PYR1]、[7196:3−c−Pr−4−CN−5−Et−PYR1]、[7197:3−CHF2−4−CN−5−Et−PYR1]、[7198:3−CF3−4−CN−5−Et−PYR1]、[7199:4−c−Pr−5−Et−PYR1]、[7200:3−F−4−c−Pr−5−Et−PYR1]、 [7101: 3-Cl-4-CF3-5-Me-PYR1], [7102: 3-Br-4-CF3-5-Me-PYR1], [7103: 3-OMe-4-CF3-5-Me -PYR1], [7104: 3-OEt-4-CF3-5-Me-PYR1], [7105: 3-CN-4-CF3-5-Me-PYR1], [7106: 3-c-Pr-4 -CF3-5-Me-PYR1], [7107: 3-CHF2-4-CF3-5-Me-PYR1], [7108: 3-CF3-4-CF3-5-Me-PYR1], [7109: 5 -Et-PYR1], [7110: 3-F-5-Et-PYR1], [7111: 3-Cl-5-Et-PYR1], [7112: 3-Br-5-Et-PYR1], [7113] : 3-OMe-5-Et-PYR ], [7114: 3-OEt-5-Et-PYR1], [7115: 3-CN-5-Et-PYR1], [7116: 3-c-Pr-5-Et-PYR1], [7117: 3 -CHF2-5-Et-PYR1], [7118: 3-CF3-5-Et-PYR1], [7119: 4-F-5-Et-PYR1], [7120: 3-F-4-F-5 -Et-PYR1], [7121: 3-Cl-4-F-5-Et-PYR1], [7122: 3-Br-4-F-5-Et-PYR1], [7123: 3-OMe-4 -F-5-Et-PYR1], [7124: 3-OEt-4-F-5-Et-PYR1], [7125: 3-CN-4-F-5-Et-PYR1], [7126: 3 -C-Pr-4-F-5-Et-PYR1], [7127: 3- HF2-4-F-5-Et-PYR1], [7128: 3-CF3-4-F-5-Et-PYR1], [7129: 4-Cl-5-Et-PYR1], [7130: 3- F-4-Cl-5-Et-PYR1], [7131: 3-Cl-4-Cl-5-Et-PYR1], [7132: 3-Br-4-Cl-5-Et-PYR1], [ 7133: 3-OMe-4-Cl-5-Et-PYR1], [7134: 3-OEt-4-Cl-5-Et-PYR1], [7135: 3-CN-4-Cl-5-Et- PYR1], [7136: 3-c-Pr-4-Cl-5-Et-PYR1], [7137: 3-CHF2-4-Cl-5-Et-PYR1], [7138: 3-CF3-4- Cl-5-Et-PYR1], [7139: 4-Br-5-Et- PYR1], [7140: 3-F-4-Br-5-Et-PYR1], [7141: 3-Cl-4-Br-5-Et-PYR1], [7142: 3-Br-4-Br- 5-Et-PYR1], [7143: 3-OMe-4-Br-5-Et-PYR1], [7144: 3-OEt-4-Br-5-Et-PYR1], [7145: 3-CN- 4-Br-5-Et-PYR1], [7146: 3-c-Pr-4-Br-5-Et-PYR1], [7147: 3-CHF2-4-Br-5-Et-PYR1], [ 7148: 3-CF3-4-Br-5-Et-PYR1], [7149: 4-Me-5-Et-PYR1], [7150: 3-F-4-Me-5-Et-PYR1], [ 7151: 3-Cl-4-Me-5-Et-PYR1], [71 2: 3-Br-4-Me-5-Et-PYR1], [7153: 3-OMe-4-Me-5-Et-PYR1], [7154: 3-OEt-4-Me-5-Et- PYR1], [7155: 3-CN-4-Me-5-Et-PYR1], [7156: 3-c-Pr-4-Me-5-Et-PYR1], [7157: 3-CHF2-4- Me-5-Et-PYR1], [7158: 3-CF3-4-Me-5-Et-PYR1], [7159: 4-Et-5-Et-PYR1], [7160: 3-F-4- Et-5-Et-PYR1], [7161: 3-Cl-4-Et-5-Et-PYR1], [7162: 3-Br-4-Et-5-Et-PYR1], [7163: 3- OMe-4-Et-5-Et-PYR1], [7164: 3-OE -4-Et-5-Et-PYR1], [7165: 3-CN-4-Et-5-Et-PYR1], [7166: 3-c-Pr-4-Et-5-Et-PYR1], [7167: 3-CHF2-4-Et-5-Et-PYR1], [7168: 3-CF3-4-Et-5-Et-PYR1], [7169: 4-OMe-5-Et-PYR1], [7170: 3-F-4-OMe-5-Et-PYR1], [7171: 3-Cl-4-OMe-5-Et-PYR1], [7172: 3-Br-4-OMe-5-Et -PYR1], [7173: 3-OMe-4-OMe-5-Et-PYR1], [7174: 3-OEt-4-OMe-5-Et-PYR1], [7175: 3-CN-4-OMe. -5-Et-PYR1], [7176: 3-c-P r-4-OMe-5-Et-PYR1], [7177: 3-CHF2-4-OMe-5-Et-PYR1], [7178: 3-CF3-4-OMe-5-Et-PYR1], [ 7179: 4-OEt-5-Et-PYR1], [7180: 3-F-4-OEt-5-Et-PYR1], [7181: 3-Cl-4-OEt-5-Et-PYR1], [ 7182: 3-Br-4-OEt-5-Et-PYR1], [7183: 3-OMe-4-OEt-5-Et-PYR1], [7184: 3-OEt-4-OEt-5-Et- PYR1], [7185: 3-CN-4-OEt-5-Et-PYR1], [7186: 3-c-Pr-4-OEt-5-Et-PYR1], [7187: 3-CHF2-4- OEt-5-Et-PYR1], [71 8: 3-CF3-4-OEt-5-Et-PYR1], [7189: 4-CN-5-Et-PYR1], [7190: 3-F-4-CN-5-Et-PYR1], [ 7191: 3-Cl-4-CN-5-Et-PYR1], [7192: 3-Br-4-CN-5-Et-PYR1], [7193: 3-OMe-4-CN-5-Et- PYR1], [7194: 3-OEt-4-CN-5-Et-PYR1], [7195: 3-CN-4-CN-5-Et-PYR1], [7196: 3-c-Pr-4- CN-5-Et-PYR1], [7197: 3-CHF2-4-CN-5-Et-PYR1], [7198: 3-CF3-4-CN-5-Et-PYR1], [7199: 4- c-Pr-5-Et-PYR1], [7200: 3-F-4- -Pr-5-Et-PYR1],
[7201:3−Cl−4−c−Pr−5−Et−PYR1]、[7202:3−Br−4−c−Pr−5−Et−PYR1]、[7203:3−OMe−4−c−Pr−5−Et−PYR1]、[7204:3−OEt−4−c−Pr−5−Et−PYR1]、[7205:3−CN−4−c−Pr−5−Et−PYR1]、[7206:3−c−Pr−4−c−Pr−5−Et−PYR1]、[7207:3−CHF2−4−c−Pr−5−Et−PYR1]、[7208:3−CF3−4−c−Pr−5−Et−PYR1]、[7209:4−CHF2−5−Et−PYR1]、[7210:3−F−4−CHF2−5−Et−PYR1]、[7211:3−Cl−4−CHF2−5−Et−PYR1]、[7212:3−Br−4−CHF2−5−Et−PYR1]、[7213:3−OMe−4−CHF2−5−Et−PYR1]、[7214:3−OEt−4−CHF2−5−Et−PYR1]、[7215:3−CN−4−CHF2−5−Et−PYR1]、[7216:3−c−Pr−4−CHF2−5−Et−PYR1]、[7217:3−CHF2−4−CHF2−5−Et−PYR1]、[7218:3−CF3−4−CHF2−5−Et−PYR1]、[7219:4−CF3−5−Et−PYR1]、[7220:3−F−4−CF3−5−Et−PYR1]、[7221:3−Cl−4−CF3−5−Et−PYR1]、[7222:3−Br−4−CF3−5−Et−PYR1]、[7223:3−OMe−4−CF3−5−Et−PYR1]、[7224:3−OEt−4−CF3−5−Et−PYR1]、[7225:3−CN−4−CF3−5−Et−PYR1]、[7226:3−c−Pr−4−CF3−5−Et−PYR1]、[7227:3−CHF2−4−CF3−5−Et−PYR1]、[7228:3−CF3−4−CF3−5−Et−PYR1]、[7229:1−Me−PYR3]、[7230:1−Me−4−F−PYR3]、[7231:1−Me−4−Cl−PYR3]、[7232:1−Me−4−Br−PYR3]、[7233:1−Me−4−Me−PYR3]、[7234:1−Me−4−Et−PYR3]、[7235:1−Me−4−OMe−PYR3]、[7236:1−Me−4−OEt−PYR3]、[7237:1−Me−4−CN−PYR3]、[7238:1−Me−4−c−Pr−PYR3]、[7239:1−Me−4−CHF2−PYR3]、[7240:1−Me−4−CF3−PYR3]、[7241:1−Me−5−F−PYR3]、[7242:1−Me−4−F−5−F−PYR3]、[7243:1−Me−4−Cl−5−F−PYR3]、[7244:1−Me−4−Br−5−F−PYR3]、[7245:1−Me−4−Me−5−F−PYR3]、[7246:1−Me−4−Et−5−F−PYR3]、[7247:1−Me−4−OMe−5−F−PYR3]、[7248:1−Me−4−OEt−5−F−PYR3]、[7249:1−Me−4−CN−5−F−PYR3]、[7250:1−Me−4−c−Pr−5−F−PYR3]、[7251:1−Me−4−CHF2−5−F−PYR3]、[7252:1−Me−4−CF3−5−F−PYR3]、[7253:1−Me−5−Cl−PYR3]、[7254:1−Me−4−F−5−Cl−PYR3]、[7255:1−Me−4−Cl−5−Cl−PYR3]、[7256:1−Me−4−Br−5−Cl−PYR3]、[7257:1−Me−4−Me−5−Cl−PYR3]、[7258:1−Me−4−Et−5−Cl−PYR3]、[7259:1−Me−4−OMe−5−Cl−PYR3]、[7260:1−Me−4−OEt−5−Cl−PYR3]、[7261:1−Me−4−CN−5−Cl−PYR3]、[7262:1−Me−4−c−Pr−5−Cl−PYR3]、[7263:1−Me−4−CHF2−6−Cl−PYR3]、[7264:1−Me−4−CF3−7−Cl−PYR3]、[7265:1−Me−5−Br−PYR3]、[7266:1−Me−4−F−5−Br−PYR3]、[7267:1−Me−4−Cl−5−Br−PYR3]、[7268:1−Me−4−Br−5−Br−PYR3]、[7269:1−Me−4−Me−5−Br−PYR3]、[7270:1−Me−4−Et−5−Br−PYR3]、[7271:1−Me−4−OMe−5−Br−PYR3]、[7272:1−Me−4−OEt−5−Br−PYR3]、[7273:1−Me−4−CN−5−Br−PYR3]、[7274:1−Me−4−c−Pr−5−Br−PYR3]、[7275:1−Me−4−CHF2−5−Br−PYR3]、[7276:1−Me−4−CF3−5−Br−PYR3]、[7277:1−Me−5−Me−PYR3]、[7278:1−Me−4−F−5−Me−PYR3]、[7279:1−Me−4−Cl−5−Me−PYR3]、[7280:1−Me−4−Br−5−Me−PYR3]、[7281:1−Me−4−Me−5−Me−PYR3]、[7282:1−Me−4−Et−5−Me−PYR3]、[7283:1−Me−4−OMe−5−Me−PYR3]、[7284:1−Me−4−OEt−5−Me−PYR3]、[7285:1−Me−4−CN−5−Me−PYR3]、[7286:1−Me−4−c−Pr−5−Me−PYR3]、[7287:1−Me−4−CHF2−5−Me−PYR3]、[7288:1−Me−4−CF3−5−Me−PYR3]、[7289:1−Me−5−Et−PYR3]、[7290:1−Me−4−F−5−Et−PYR3]、[7291:1−Me−4−Cl−5−Et−PYR3]、[7292:1−Me−4−Br−5−Et−PYR3]、[7293:1−Me−4−Me−5−Et−PYR3]、[7294:1−Me−4−Et−5−Et−PYR3]、[7295:1−Me−4−OMe−5−Et−PYR3]、[7296:1−Me−4−OEt−5−Et−PYR3]、[7297:1−Me−4−CN−5−Et−PYR3]、[7298:1−Me−4−c−Pr−5−Et−PYR3]、[7299:1−Me−4−CHF2−5−Et−PYR3]、[7300:1−Me−4−CF3−5−Et−PYR3]、 [7201: 3-Cl-4-c-Pr-5-Et-PYR1], [7202: 3-Br-4-c-Pr-5-Et-PYR1], [7203: 3-OMe-4-c -Pr-5-Et-PYR1], [7204: 3-OEt-4-c-Pr-5-Et-PYR1], [7205: 3-CN-4-c-Pr-5-Et-PYR1], [7206: 3-c-Pr-4-c-Pr-5-Et-PYR1], [7207: 3-CHF2-4-c-Pr-5-Et-PYR1], [7208: 3-CF3-4 -C-Pr-5-Et-PYR1], [7209: 4-CHF2-5-Et-PYR1], [7210: 3-F-4-CHF2-5-Et-PYR1], [7211: 3-Cl -4-CHF2-5-Et-PYR1], [7212: 3-Br-4- HF2-5-Et-PYR1], [7213: 3-OMe-4-CHF2-5-Et-PYR1], [7214: 3-OEt-4-CHF2-5-Et-PYR1], [7215: 3- CN-4-CHF2-5-Et-PYR1], [7216: 3-c-Pr-4-CHF2-5-Et-PYR1], [7217: 3-CHF2-4-CHF2-5-Et-PYR1] [7218: 3-CF3-4-CHF2-5-Et-PYR1], [7219: 4-CF3-5-Et-PYR1], [7220: 3-F-4-CF3-5-Et-PYR1] [7221: 3-Cl-4-CF3-5-Et-PYR1], [7222: 3-Br-4-CF3-5-Et-PYR1], [7223: 3-OMe-4-CF3-5. Et-PYR1], [ 224: 3-OEt-4-CF3-5-Et-PYR1], [7225: 3-CN-4-CF3-5-Et-PYR1], [7226: 3-c-Pr-4-CF3-5 Et-PYR1], [7227: 3-CHF2-4-CF3-5-Et-PYR1], [7228: 3-CF3-4-CF3-5-Et-PYR1], [7229: 1-Me-PYR3] [7230: 1-Me-4-F-PYR3], [7231: 1-Me-4-Cl-PYR3], [7232: 1-Me-4-Br-PYR3], [7233: 1-Me- 4-Me-PYR3], [7234: 1-Me-4-Et-PYR3], [7235: 1-Me-4-OMe-PYR3], [7236: 1-Me-4-OEt-PYR3], [ 7237: 1-Me-4-CN-P YR3], [7238: 1-Me-4-c-Pr-PYR3], [7239: 1-Me-4-CHF2-PYR3], [7240: 1-Me-4-CF3-PYR3], [7241: 1-Me-5-F-PYR3], [7242: 1-Me-4-F-5-F-PYR3], [7243: 1-Me-4-Cl-5-F-PYR3], [7244: 1-Me-4-Br-5-F-PYR3], [7245: 1-Me-4-Me-5-F-PYR3], [7246: 1-Me-4-Et-5-F-PYR3] [7247: 1-Me-4-OMe-5-F-PYR3], [7248: 1-Me-4-OEt-5-F-PYR3], [7249: 1-Me-4-CN-5. F-PYR3], [7250: 1-Me-4-c-Pr-5-F-PYR3] [7251: 1-Me-4-CHF2-5-F-PYR3], [7252: 1-Me-4-CF3-5-F-PYR3], [7253: 1-Me-5-Cl-PYR3], [7254: 1-Me-4-F-5-Cl-PYR3], [7255: 1-Me-4-Cl-5-Cl-PYR3], [7256: 1-Me-4-Br-5-Cl -PYR3], [7257: 1-Me-4-Me-5-Cl-PYR3], [7258: 1-Me-4-Et-5-Cl-PYR3], [7259: 1-Me-4-OMe. -5-Cl-PYR3], [7260: 1-Me-4-OEt-5-Cl-PYR3], [7261: 1-Me-4-CN-5-Cl-PYR3], [7262: 1-Me -4-c-Pr-5-Cl-PYR3], [7263: 1-M -4-CHF2-6-Cl-PYR3], [7264: 1-Me-4-CF3-7-Cl-PYR3], [7265: 1-Me-5-Br-PYR3], [7266: 1-Me. -4-F-5-Br-PYR3], [7267: 1-Me-4-Cl-5-Br-PYR3], [7268: 1-Me-4-Br-5-Br-PYR3], [7269. : 1-Me-4-Me-5-Br-PYR3], [7270: 1-Me-4-Et-5-Br-PYR3], [7271: 1-Me-4-OMe-5-Br-PYR3] ], [7272: 1-Me-4-OEt-5-Br-PYR3], [7273: 1-Me-4-CN-5-Br-PYR3], [7274: 1-Me-4-c-Pr. -5-Br-PYR3], [7275: 1-Me-4-CHF2- 5-Br-PYR3], [7276: 1-Me-4-CF3-5-Br-PYR3], [7277: 1-Me-5-Me-PYR3], [7278: 1-Me-4-F- 5-Me-PYR3], [7279: 1-Me-4-Cl-5-Me-PYR3], [7280: 1-Me-4-Br-5-Me-PYR3], [7281: 1-Me- 4-Me-5-Me-PYR3], [7282: 1-Me-4-Et-5-Me-PYR3], [7283: 1-Me-4-OMe-5-Me-PYR3], [7284: 1-Me-4-OEt-5-Me-PYR3], [7285: 1-Me-4-CN-5-Me-PYR3], [7286: 1-Me-4-c-Pr-5-Me- PYR3], [7287: 1-Me-4-CHF2-5-Me-PYR ], [7288: 1-Me-4-CF3-5-Me-PYR3], [7289: 1-Me-5-Et-PYR3], [7290: 1-Me-4-F-5-Et-PYR3]. ], [7291: 1-Me-4-Cl-5-Et-PYR3], [7292: 1-Me-4-Br-5-Et-PYR3], [7293: 1-Me-4-Me-5]. -Et-PYR3], [7294: 1-Me-4-Et-5-Et-PYR3], [7295: 1-Me-4-OMe-5-Et-PYR3], [7296: 1-Me-4. -OEt-5-Et-PYR3], [7297: 1-Me-4-CN-5-Et-PYR3], [7298: 1-Me-4-c-Pr-5-Et-PYR3], [7299 : 1-Me-4-CHF2-5-Et-PYR3], [7300 1-Me-4-CF3-5-Et-PYR3],
[7301:1−Me−5−OMe−PYR3]、[7302:1−Me−4−F−5−OMe−PYR3]、[7303:1−Me−4−Cl−5−OMe−PYR3]、[7304:1−Me−4−Br−5−OMe−PYR3]、[7305:1−Me−4−Me−5−OMe−PYR3]、[7306:1−Me−4−Et−5−OMe−PYR3]、[7307:1−Me−4−OMe−5−OMe−PYR3]、[7308:1−Me−4−OEt−5−OMe−PYR3]、[7309:1−Me−4−CN−5−OMe−PYR3]、[7310:1−Me−4−c−Pr−5−OMe−PYR3]、[7311:1−Me−4−CHF2−5−OMe−PYR3]、[7312:1−Me−4−CF3−5−OMe−PYR3]、[7313:1−Me−5−OEt−PYR3]、[7314:1−Me−4−F−5−OEt−PYR3]、[7315:1−Me−4−Cl−5−OEt−PYR3]、[7316:1−Me−4−Br−5−OEt−PYR3]、[7317:1−Me−4−Me−5−OEt−PYR3]、[7318:1−Me−4−Et−5−OEt−PYR3]、[7319:1−Me−4−OMe−5−OEt−PYR3]、[7320:1−Me−4−OEt−5−OEt−PYR3]、[7321:1−Me−4−CN−5−OEt−PYR3]、[7322:1−Me−4−c−Pr−5−OEt−PYR3]、[7323:1−Me−4−CHF2−5−OEt−PYR3]、[7324:1−Me−4−CF3−5−OEt−PYR3]、[7325:1−Me−5−CN−PYR3]、[7326:1−Me−4−F−5−CN−PYR3]、[7327:1−Me−4−Cl−5−CN−PYR3]、[7328:1−Me−4−Br−5−CN−PYR3]、[7329:1−Me−4−Me−5−CN−PYR3]、[7330:1−Me−4−Et−5−CN−PYR3]、[7331:1−Me−4−OMe−5−CN−PYR3]、[7332:1−Me−4−OEt−5−CN−PYR3]、[7333:1−Me−4−CN−5−CN−PYR3]、[7334:1−Me−4−c−Pr−5−CN−PYR3]、[7335:1−Me−4−CHF2−5−CN−PYR3]、[7336:1−Me−4−CF3−5−CN−PYR3]、[7337:1−Me−5−c−Pr−PYR3]、[7338:1−Me−4−F−5−c−Pr−PYR3]、[7339:1−Me−4−Cl−5−c−Pr−PYR3]、[7340:1−Me−4−Br−5−c−Pr−PYR3]、[7341:1−Me−4−Me−5−c−Pr−PYR3]、[7342:1−Me−4−Et−5−c−Pr−PYR3]、[7343:1−Me−4−OMe−5−c−Pr−PYR3]、[7344:1−Me−4−OEt−5−c−Pr−PYR3]、[7345:1−Me−4−CN−5−c−Pr−PYR3]、[7346:1−Me−4−c−Pr−5−c−Pr−PYR3]、[7347:1−Me−4−CHF2−5−c−Pr−PYR3]、[7348:1−Me−4−CF3−5−c−Pr−PYR3]、[7349:1−Me−5−CHF2−PYR3]、[7350:1−Me−4−F−5−CHF2−PYR3]、[7351:1−Me−4−Cl−5−CHF2−PYR3]、[7352:1−Me−4−Br−5−CHF2−PYR3]、[7353:1−Me−4−Me−5−CHF2−PYR3]、[7354:1−Me−4−Et−5−CHF2−PYR3]、[7355:1−Me−4−OMe−5−CHF2−PYR3]、[7356:1−Me−4−OEt−5−CHF2−PYR3]、[7357:1−Me−4−CN−5−CHF2−PYR3]、[7358:1−Me−4−c−Pr−5−CHF2−PYR3]、[7359:1−Me−4−CHF2−5−CHF2−PYR3]、[7360:1−Me−4−CF3−5−CHF2−PYR3]、[7361:1−Me−5−CF3−PYR3]、[7362:1−Me−4−F−5−CF3−PYR3]、[7363:1−Me−4−Cl−5−CF3−PYR3]、[7364:1−Me−4−Br−5−CF3−PYR3]、[7365:1−Me−4−Me−5−CF3−PYR3]、[7366:1−Me−4−Et−5−CF3−PYR3]、[7367:1−Me−4−OMe−5−CF3−PYR3]、[7368:1−Me−4−OEt−5−CF3−PYR3]、[7369:1−Me−4−CN−5−CF3−PYR3]、[7370:1−Me−4−c−Pr−5−CF3−PYR3]、[7371:1−Me−4−CHF2−5−CF3−PYR3]、[7372:1−Me−4−CF3−5−CF3−PYR3]、[7373:1−Me−5−OPr−PYR3]、[7374:1−Me−4−F−5−OPr−PYR3]、[7375:1−Me−4−Cl−5−OPr−PYR3]、[7376:1−Me−4−Br−5−OPr−PYR3]、[7377:1−Me−4−Me−5−OPr−PYR3]、[7378:1−Me−4−Et−5−OPr−PYR3]、[7379:1−Me−4−OMe−5−OPr−PYR3]、[7380:1−Me−4−OEt−5−OPr−PYR3]、[7381:1−Me−4−CN−5−OPr−PYR3]、[7382:1−Me−4−c−Pr−5−OPr−PYR3]、[7383:1−Me−4−CHF2−5−OPr−PYR3]、[7384:1−Me−4−CF3−5−OPr−PYR3]、[7385:1−Me−5−OCH2CH=CH2−PYR3]、[7386:1−Me−4−F−5−OCH2CH=CH2−PYR3]、[7387:1−Me−4−Cl−5−OCH2CH=CH2−PYR3]、[7388:1−Me−4−Br−5−OCH2CH=CH2−PYR3]、[7389:1−Me−4−Me−5−OCH2CH=CH2−PYR3]、[7390:1−Me−4−Et−5−OCH2CH=CH2−PYR3]、[7391:1−Me−4−OMe−5−OCH2CH=CH2−PYR3]、[7392:1−Me−4−OEt−5−OCH2CH=CH2−PYR3]、[7393:1−Me−4−CN−5−OCH2CH=CH2−PYR3]、[7394:1−Me−4−c−Pr−5−OCH2CH=CH2−PYR3]、[7395:1−Me−4−CHF2−5−OCH2CH=CH2−PYR3]、[7396:1−Me−4−CF3−5−OCH2CH=CH2−PYR3]、[7397:1−Me−5−OCH2CH=CCl2−PYR3]、[7398:1−Me−4−F−5−OCH2CH=CCl2−PYR3]、[7399:1−Me−4−Cl−5−OCH2CH=CCl2−PYR3]、[7400:1−Me−4−Br−5−OCH2CH=CCl2−PYR3]、 [7301: 1-Me-5-OMe-PYR3], [7302: 1-Me-4-F-5-OMe-PYR3], [7303: 1-Me-4-Cl-5-OMe-PYR3], [7304: 1-Me-4-Br-5-OMe-PYR3], [7305: 1-Me-4-Me-5-OMe-PYR3], [7306: 1-Me-4-Et-5-OMe -PYR3], [7307: 1-Me-4-OMe-5-OMe-PYR3], [7308: 1-Me-4-OEt-5-OMe-PYR3], [7309: 1-Me-4-CN. -5-OMe-PYR3], [7310: 1-Me-4-c-Pr-5-OMe-PYR3], [7311: 1-Me-4-CHF2-5-OMe-PYR3], [7312: 1 -Me-4-CF3-5-OMe-PY 3], [7313: 1-Me-5-OEt-PYR3], [7314: 1-Me-4-F-5-OEt-PYR3], [7315: 1-Me-4-Cl-5-OEt- PYR3], [7316: 1-Me-4-Br-5-OEt-PYR3], [7317: 1-Me-4-Me-5-OEt-PYR3], [7318: 1-Me-4-Et- 5-OEt-PYR3], [7319: 1-Me-4-OMe-5-OEt-PYR3], [7320: 1-Me-4-OEt-5-OEt-PYR3], [7321: 1-Me- 4-CN-5-OEt-PYR3], [7322: 1-Me-4-c-Pr-5-OEt-PYR3], [7323: 1-Me-4-CHF2-5-OEt-PYR3], [ 7324: 1-Me-4-CF3-5-OE -PYR3], [7325: 1-Me-5-CN-PYR3], [7326: 1-Me-4-F-5-CN-PYR3], [7327: 1-Me-4-Cl-5-CN. -PYR3], [7328: 1-Me-4-Br-5-CN-PYR3], [7329: 1-Me-4-Me-5-CN-PYR3], [7330: 1-Me-4-Et. -5-CN-PYR3], [7331: 1-Me-4-OMe-5-CN-PYR3], [7332: 1-Me-4-OEt-5-CN-PYR3], [7333: 1-Me. -4-CN-5-CN-PYR3], [7334: 1-Me-4-c-Pr-5-CN-PYR3], [7335: 1-Me-4-CHF2-5-CN-PYR3], [7336: 1-Me-4-CF3-5-CN-PYR3], [ 7337: 1-Me-5-c-Pr-PYR3], [7338: 1-Me-4-F-5-c-Pr-PYR3], [7339: 1-Me-4-Cl-5-c- Pr-PYR3], [7340: 1-Me-4-Br-5-c-Pr-PYR3], [7341: 1-Me-4-Me-5-c-Pr-PYR3], [7341: 1 Me-4-Et-5-c-Pr-PYR3], [7343: 1-Me-4-OMe-5-c-Pr-PYR3], [7344: 1-Me-4-OEt-5-c- Pr-PYR3], [7345: 1-Me-4-CN-5-c-Pr-PYR3], [7346: 1-Me-4-c-Pr-5-c-Pr-PYR3], [7347: 1-Me-4-CHF2-5-c-Pr-PYR3], [7348: 1-Me-4-CF -5-c-Pr-PYR3], [7349: 1-Me-5-CHF2-PYR3], [7350: 1-Me-4-F-5-CHF2-PYR3], [7351: 1-Me-4. -Cl-5-CHF2-PYR3], [7352: 1-Me-4-Br-5-CHF2-PYR3], [7353: 1-Me-4-Me-5-CHF2-PYR3], [7354: 1. -Me-4-Et-5-CHF2-PYR3], [7355: 1-Me-4-OMe-5-CHF2-PYR3], [7356: 1-Me-4-OEt-5-CHF2-PYR3], [7357: 1-Me-4-CN-5-CHF2-PYR3], [7358: 1-Me-4-c-Pr-5-CHF2-PYR3], [7359: 1-Me-4-CHF2-5 -CHF2-PYR3] [7360: 1-Me-4-CF3-5-CHF2-PYR3], [7361: 1-Me-5-CF3-PYR3], [7362: 1-Me-4-F-5-CF3-PYR3], [7363: 1-Me-4-Cl-5-CF3-PYR3], [7364: 1-Me-4-Br-5-CF3-PYR3], [7365: 1-Me-4-Me-5-CF3 -PYR3], [7366: 1-Me-4-Et-5-CF3-PYR3], [7367: 1-Me-4-OMe-5-CF3-PYR3], [7368: 1-Me-4-OEt. -5-CF3-PYR3], [7369: 1-Me-4-CN-5-CF3-PYR3], [7370: 1-Me-4-c-Pr-5-CF3-PYR3], [7371: 1 -Me-4-CHF2-5-CF3-P YR3], [7372: 1-Me-4-CF3-5-CF3-PYR3], [7373: 1-Me-5-OPr-PYR3], [7374: 1-Me-4-F-5-OPr- PYR3], [7375: 1-Me-4-Cl-5-OPr-PYR3], [7376: 1-Me-4-Br-5-OPr-PYR3], [7377: 1-Me-4-Me- 5-OPr-PYR3], [7378: 1-Me-4-Et-5-OPr-PYR3], [7379: 1-Me-4-OMe-5-OPr-PYR3], [7380: 1-Me- 4-OEt-5-OPr-PYR3], [7381: 1-Me-4-CN-5-OPr-PYR3], [7342: 1-Me-4-c-Pr-5-OPr-PYR3], [ 7383: 1-Me-4-CHF2-5-O r-PYR3], [7384: 1-Me-4-CF3-5-OPr-PYR3], [7385: 1-Me-5-OCH2CH = CH2-PYR3], [7386: 1-Me-4-F- 5-OCH2CH = CH2-PYR3], [7387: 1-Me-4-Cl-5-OCH2CH = CH2-PYR3], [7388: 1-Me-4-Br-5-OCH2CH = CH2-PYR3], [ 7389: 1-Me-4-Me-5-OCH2CH = CH2-PYR3], [7390: 1-Me-4-Et-5-OCH2CH = CH2-PYR3], [7391: 1-Me-4-OMe- 5-OCH2CH = CH2-PYR3], [7392: 1-Me-4-OEt-5-OCH2CH = CH2-PYR3], [7393: 1-Me-4-CN-5-O. H2CH = CH2-PYR3], [7394: 1-Me-4-c-Pr-5-OCH2CH = CH2-PYR3], [7395: 1-Me-4-CHF2-5-OCH2CH = CH2-PYR3], [ 7396: 1-Me-4-CF3-5-OCH2CH = CH2-PYR3], [7397: 1-Me-5-OCH2CH = CCl2-PYR3], [7398: 1-Me-4-F-5-OCH2CH = CCl2-PYR3], [7399: 1-Me-4-Cl-5-OCH2CH = CCl2-PYR3], [7400: 1-Me-4-Br-5-OCH2CH = CCl2-PYR3],
[7401:1−Me−4−Me−5−OCH2CH=CCl2−PYR3]、[7402:1−Me−4−Et−5−OCH2CH=CCl2−PYR3]、[7403:1−Me−4−OMe−5−OCH2CH=CCl2−PYR3]、[7404:1−Me−4−OEt−5−OCH2CH=CCl2−PYR3]、[7405:1−Me−4−CN−5−OCH2CH=CCl2−PYR3]、[7406:1−Me−4−c−Pr−5−OCH2CH=CCl2−PYR3]、[7407:1−Me−4−CHF2−5−OCH2CH=CCl2−PYR3]、[7408:1−Me−4−CF3−5−OCH2CH=CCl2−PYR3]、[7409:1−Me−5−OCH2C≡CH−PYR3]、[7410:1−Me−4−F−5−OCH2C≡CH−PYR3]、[7411:1−Me−4−Cl−5−OCH2C≡CH−PYR3]、[7412:1−Me−4−Br−5−OCH2C≡CH−PYR3]、[7413:1−Me−4−Me−5−OCH2C≡CH−PYR3]、[7414:1−Me−4−Et−5−OCH2C≡CH−PYR3]、[7415:1−Me−4−OMe−5−OCH2C≡CH−PYR3]、[7416:1−Me−4−OEt−5−OCH2C≡CH−PYR3]、[7417:1−Me−4−CN−5−OCH2C≡CH−PYR3]、[7418:1−Me−4−c−Pr−5−OCH2C≡CH−PYR3]、[7419:1−Me−4−CHF2−5−OCH2C≡CH−PYR3]、[7420:1−Me−4−CF3−5−OCH2C≡CH−PYR3]、[7421:1−Me−5−OCH2CF3−PYR3]、[7422:1−Me−4−F−5−OCH2CF3−PYR3]、[7423:1−Me−4−Cl−5−OCH2CF3−PYR3]、[7424:1−Me−4−Br−5−OCH2CF3−PYR3]、[7425:1−Me−4−Me−5−OCH2CF3−PYR3]、[7426:1−Me−4−Et−5−OCH2CF3−PYR3]、[7427:1−Me−4−OMe−5−OCH2CF3−PYR3]、[7428:1−Me−4−OEt−5−OCH2CF3−PYR3]、[7429:1−Me−4−CN−5−OCH2CF3−PYR3]、[7430:1−Me−4−c−Pr−5−OCH2CF3−PYR3]、[7431:1−Me−4−CHF2−5−OCH2CF3−PYR3]、[7432:1−Me−4−CF3−5−OCH2CF3−PYR3]、[7433:1−Me−5−CH2OCH3−PYR3]、[7434:1−Me−4−F−5−CH2OCH3−PYR3]、[7435:1−Me−4−Cl−5−CH2OCH3−PYR3]、[7436:1−Me−4−Br−5−CH2OCH3−PYR3]、[7437:1−Me−4−Me−5−CH2OCH3−PYR3]、[7438:1−Me−4−Et−5−CH2OCH3−PYR3]、[7439:1−Me−4−OMe−5−CH2OCH3−PYR3]、[7440:1−Me−4−OEt−5−CH2OCH3−PYR3]、[7441:1−Me−4−CN−5−CH2OCH3−PYR3]、[7442:1−Me−4−c−Pr−5−CH2OCH3−PYR3]、[7443:1−Me−4−CHF2−5−CH2OCH3−PYR3]、[7444:1−Me−4−CF3−5−CH2OCH3−PYR3]、[7445:1−Et−PYR3]、[7446:1−Et−4−F−PYR3]、[7447:1−Et−4−Cl−PYR3]、[7448:1−Et−4−Br−PYR3]、[7449:1−Et−4−Me−PYR3]、[7450:1−Et−4−Et−PYR3]、[7451:1−Et−4−OMe−PYR3]、[7452:1−Et−4−OEt−PYR3]、[7453:1−Et−4−CN−PYR3]、[7454:1−Et−4−c−Pr−PYR3]、[7455:1−Et−4−CHF2−PYR3]、[7456:1−Et−4−CF3−PYR3]、[7457:1−Et−5−F−PYR3]、[7458:1−Et−4−F−5−F−PYR3]、[7459:1−Et−4−Cl−5−F−PYR3]、[7460:1−Et−4−Br−5−F−PYR3]、[7461:1−Et−4−Me−5−F−PYR3]、[7462:1−Et−4−Et−5−F−PYR3]、[7463:1−Et−4−OMe−5−F−PYR3]、[7464:1−Et−4−OEt−5−F−PYR3]、[7465:1−Et−4−CN−5−F−PYR3]、[7466:1−Et−4−c−Pr−5−F−PYR3]、[7467:1−Et−4−CHF2−5−F−PYR3]、[7468:1−Et−4−CF3−5−F−PYR3]、[7469:1−Et−5−Cl−PYR3]、[7470:1−Et−4−F−5−Cl−PYR3]、[7471:1−Et−4−Cl−5−Cl−PYR3]、[7472:1−Et−4−Br−5−Cl−PYR3]、[7473:1−Et−4−Me−5−Cl−PYR3]、[7474:1−Et−4−Et−5−Cl−PYR3]、[7475:1−Et−4−OMe−5−Cl−PYR3]、[7476:1−Et−4−OEt−5−Cl−PYR3]、[7477:1−Et−4−CN−5−Cl−PYR3]、[7478:1−Et−4−c−Pr−5−Cl−PYR3]、[7479:1−Et−4−CHF2−5−Cl−PYR3]、[7480:1−Et−4−CF3−5−Cl−PYR3]、[7481:1−Et−5−Br−PYR3]、[7482:1−Et−4−F−5−Br−PYR3]、[7483:1−Et−4−Cl−5−Br−PYR3]、[7484:1−Et−4−Br−5−Br−PYR3]、[7485:1−Et−4−Me−5−Br−PYR3]、[7486:1−Et−4−Et−5−Br−PYR3]、[7487:1−Et−4−OMe−5−Br−PYR3]、[7488:1−Et−4−OEt−5−Br−PYR3]、[7489:1−Et−4−CN−5−Br−PYR3]、[7490:1−Et−4−c−Pr−5−Br−PYR3]、[7491:1−Et−4−CHF2−5−Br−PYR3]、[7492:1−Et−4−CF3−5−Br−PYR3]、[7493:1−Et−5−Me−PYR3]、[7494:1−Et−4−F−5−Me−PYR3]、[7495:1−Et−4−Cl−5−Me−PYR3]、[7496:1−Et−4−Br−5−Me−PYR3]、[7497:1−Et−4−Me−5−Me−PYR3]、[7498:1−Et−4−Et−5−Me−PYR3]、[7499:1−Et−4−OMe−5−Me−PYR3]、[7500:1−Et−4−OEt−5−Me−PYR3]、 [7401: 1-Me-4-Me-5-OCH2CH = CCl2-PYR3], [7402: 1-Me-4-Et-5-OCH2CH = CCl2-PYR3], [7403: 1-Me-4-OMe -5-OCH2CH = CCl2-PYR3], [7404: 1-Me-4-OEt-5-OCH2CH = CCl2-PYR3], [7405: 1-Me-4-CN-5-OCH2CH = CCl2-PYR3], [7406: 1-Me-4-c-Pr-5-OCH2CH = CCl2-PYR3], [7407: 1-Me-4-CHF2-5-OCH2CH = CCl2-PYR3], [7408: 1-Me-4 -CF3-5-OCH2CH = CCl2-PYR3], [7409: 1-Me-5-OCH2C≡CH-PYR3], [7410: 1-Me 4-F-5-OCH2C≡CH-PYR3], [7411: 1-Me-4-Cl-5-OCH2C≡CH-PYR3], [7412: 1-Me-4-Br-5-OCH2C≡CH— PYR3], [7413: 1-Me-4-Me-5-OCH2C≡CH-PYR3], [7414: 1-Me-4-Et-5-OCH2C≡CH-PYR3], [7415: 1-Me- 4-OMe-5-OCH2C≡CH-PYR3], [7416: 1-Me-4-OEt-5-OCH2C≡CH-PYR3], [7417: 1-Me-4-CN-5-OCH2C≡CH— PYR3], [7418: 1-Me-4-c-Pr-5-OCH2C≡CH-PYR3], [7419: 1-Me-4-CHF2-5-OCH2C≡CH-PYR3], [7420: 1- e-4-CF3-5-OCH2C≡CH-PYR3], [7421: 1-Me-5-OCH2CF3-PYR3], [7422: 1-Me-4-F-5-OCH2CF3-PYR3], [7423: 1-Me-4-Cl-5-OCH2CF3-PYR3], [7424: 1-Me-4-Br-5-OCH2CF3-PYR3], [7425: 1-Me-4-Me-5-OCH2CF3-PYR3] [7426: 1-Me-4-Et-5-OCH2CF3-PYR3], [7427: 1-Me-4-OMe-5-OCH2CF3-PYR3], [7428: 1-Me-4-OEt-5 OCH2CF3-PYR3], [7429: 1-Me-4-CN-5-OCH2CF3-PYR3], [7430: 1-Me-4-c-Pr-5-OCH2 CF3-PYR3], [7431: 1-Me-4-CHF2-5-OCH2CF3-PYR3], [7432: 1-Me-4-CF3-5-OCH2CF3-PYR3], [7433: 1-Me-5 CH2OCH3-PYR3], [7434: 1-Me-4-F-5-CH2OCH3-PYR3], [7435: 1-Me-4-Cl-5-CH2OCH3-PYR3], [7436: 1-Me-4-. Br-5-CH2OCH3-PYR3], [7437: 1-Me-4-Me-5-CH2OCH3-PYR3], [7438: 1-Me-4-Et-5-CH2OCH3-PYR3], [7439: 1- Me-4-OMe-5-CH2OCH3-PYR3], [7440: 1-Me-4-OEt-5-CH2OCH3-PYR3], [744] : 1-Me-4-CN-5-CH2OCH3-PYR3], [7442: 1-Me-4-c-Pr-5-CH2OCH3-PYR3], [7443: 1-Me-4-CHF2-5-CH2OCH3 -PYR3], [7444: 1-Me-4-CF3-5-CH2OCH3-PYR3], [7445: 1-Et-PYR3], [7446: 1-Et-4-F-PYR3], [7447: 1. -Et-4-Cl-PYR3], [7448: 1-Et-4-Br-PYR3], [7449: 1-Et-4-Me-PYR3], [7450: 1-Et-4-Et-PYR3] ], [7451: 1-Et-4-OMe-PYR3], [7452: 1-Et-4-OEt-PYR3], [7453: 1-Et-4-CN-PYR3], [7454: 1-Et. 4-c-Pr-PYR3], [7455: 1-Et-4-CHF2-PYR3], [7456: 1-Et-4-CF3-PYR3], [7457: 1-Et-5-F-PYR3] [7458: 1-Et-4-F-5-F-PYR3], [7459: 1-Et-4-Cl-5-F-PYR3], [7460: 1-Et-4-Br-5-5]. F-PYR3], [7461: 1-Et-4-Me-5-F-PYR3], [7462: 1-Et-4-Et-5-F-PYR3], [7463: 1-Et-4- OMe-5-F-PYR3], [7464: 1-Et-4-OEt-5-F-PYR3], [7465: 1-Et-4-CN-5-F-PYR3], [7466: 1- Et-4-c-Pr-5-F-PYR3], [7467: 1-Et-4-CH F2-5-F-PYR3], [7468: 1-Et-4-CF3-5-F-PYR3], [7469: 1-Et-5-Cl-PYR3], [7470: 1-Et-4- F-5-Cl-PYR3], [7471: 1-Et-4-Cl-5-Cl-PYR3], [7472: 1-Et-4-Br-5-Cl-PYR3], [7473: 1- Et-4-Me-5-Cl-PYR3], [7474: 1-Et-4-Et-5-Cl-PYR3], [7475: 1-Et-4-OMe-5-Cl-PYR3], [ 7476: 1-Et-4-OEt-5-Cl-PYR3], [7477: 1-Et-4-CN-5-Cl-PYR3], [7478: 1-Et-4-c-Pr-5-5 Cl-PYR3], [7479: 1-Et-4-CHF2-5-Cl-PY 3], [7480: 1-Et-4-CF3-5-Cl-PYR3], [7481: 1-Et-5-Br-PYR3], [7482: 1-Et-4-F-5-Br- PYR3], [7483: 1-Et-4-Cl-5-Br-PYR3], [7484: 1-Et-4-Br-5-Br-PYR3], [7485: 1-Et-4-Me- 5-Br-PYR3], [7486: 1-Et-4-Et-5-Br-PYR3], [7487: 1-Et-4-OMe-5-Br-PYR3], [7488: 1-Et- 4-OEt-5-Br-PYR3], [7489: 1-Et-4-CN-5-Br-PYR3], [7490: 1-Et-4-c-Pr-5-Br-PYR3], [ 7491: 1-Et-4-CHF2-5-Br-PYR3], [749 : 1-Et-4-CF3-5-Br-PYR3], [7493: 1-Et-5-Me-PYR3], [7494: 1-Et-4-F-5-Me-PYR3], [7495. : 1-Et-4-Cl-5-Me-PYR3], [7496: 1-Et-4-Br-5-Me-PYR3], [7497: 1-Et-4-Me-5-Me-PYR3]. ], [7498: 1-Et-4-Et-5-Me-PYR3], [7499: 1-Et-4-OMe-5-Me-PYR3], [7500: 1-Et-4-OEt-5 -Me-PYR3],
[7501:1−Et−4−CN−5−Me−PYR3]、[7502:1−Et−4−c−Pr−5−Me−PYR3]、[7503:1−Et−4−CHF2−5−Me−PYR3]、[7504:1−Et−4−CF3−5−Me−PYR3]、[7505:1−Et−5−Et−PYR3]、[7506:1−Et−4−F−5−Et−PYR3]、[7507:1−Et−4−Cl−5−Et−PYR3]、[7508:1−Et−4−Br−5−Et−PYR3]、[7509:1−Et−4−Me−5−Et−PYR3]、[7510:1−Et−4−Et−5−Et−PYR3]、[7511:1−Et−4−OMe−5−Et−PYR3]、[7512:1−Et−4−OEt−5−Et−PYR3]、[7513:1−Et−4−CN−5−Et−PYR3]、[7514:1−Et−4−c−Pr−5−Et−PYR3]、[7515:1−Et−4−CHF2−5−Et−PYR3]、[7516:1−Et−4−CF3−5−Et−PYR3]、[7517:1−Et−5−OMe−PYR3]、[7518:1−Et−4−F−5−OMe−PYR3]、[7519:1−Et−4−Cl−5−OMe−PYR3]、[7520:1−Et−4−Br−5−OMe−PYR3]、[7521:1−Et−4−Me−5−OMe−PYR3]、[7522:1−Et−4−Et−5−OMe−PYR3]、[7523:1−Et−4−OMe−5−OMe−PYR3]、[7524:1−Et−4−OEt−5−OMe−PYR3]、[7525:1−Et−4−CN−5−OMe−PYR3]、[7526:1−Et−4−c−Pr−5−OMe−PYR3]、[7527:1−Et−4−CHF2−5−OMe−PYR3]、[7528:1−Et−4−CF3−5−OMe−PYR3]、[7529:1−Et−5−OEt−PYR3]、[7530:1−Et−4−F−5−OEt−PYR3]、[7531:1−Et−4−Cl−5−OEt−PYR3]、[7532:1−Et−4−Br−5−OEt−PYR3]、[7533:1−Et−4−Me−5−OEt−PYR3]、[7534:1−Et−4−Et−5−OEt−PYR3]、[7535:1−Et−4−OMe−5−OEt−PYR3]、[7536:1−Et−4−OEt−5−OEt−PYR3]、[7537:1−Et−4−CN−5−OEt−PYR3]、[7538:1−Et−4−c−Pr−5−OEt−PYR3]、[7539:1−Et−4−CHF2−5−OEt−PYR3]、[7540:1−Et−4−CF3−5−OEt−PYR3]、[7541:1−Et−5−CN−PYR3]、[7542:1−Et−4−F−5−CN−PYR3]、[7543:1−Et−4−Cl−5−CN−PYR3]、[7544:1−Et−4−Br−5−CN−PYR3]、[7545:1−Et−4−Me−5−CN−PYR3]、[7546:1−Et−4−Et−5−CN−PYR3]、[7547:1−Et−4−OMe−5−CN−PYR3]、[7548:1−Et−4−OEt−5−CN−PYR3]、[7549:1−Et−4−CN−5−CN−PYR3]、[7550:1−Et−4−c−Pr−5−CN−PYR3]、[7551:1−Et−4−CHF2−5−CN−PYR3]、[7552:1−Et−4−CF3−5−CN−PYR3]、[7553:1−Et−5−c−Pr−PYR3]、[7554:1−Et−4−F−5−c−Pr−PYR3]、[7555:1−Et−4−Cl−5−c−Pr−PYR3]、[7556:1−Et−4−Br−5−c−Pr−PYR3]、[7557:1−Et−4−Me−5−c−Pr−PYR3]、[7558:1−Et−4−Et−5−c−Pr−PYR3]、[7559:1−Et−4−OMe−5−c−Pr−PYR3]、[7560:1−Et−4−OEt−5−c−Pr−PYR3]、[7561:1−Et−4−CN−5−c−Pr−PYR3]、[7562:1−Et−4−c−Pr−5−c−Pr−PYR3]、[7563:1−Et−4−CHF2−5−c−Pr−PYR3]、[7564:1−Et−4−CF3−5−c−Pr−PYR3]、[7565:1−Et−5−CHF2−PYR3]、[7566:1−Et−4−F−5−CHF2−PYR3]、[7567:1−Et−4−Cl−5−CHF2−PYR3]、[7568:1−Et−4−Br−5−CHF2−PYR3]、[7569:1−Et−4−Me−5−CHF2−PYR3]、[7570:1−Et−4−Et−5−CHF2−PYR3]、[7571:1−Et−4−OMe−5−CHF2−PYR3]、[7572:1−Et−4−OEt−5−CHF2−PYR3]、[7573:1−Et−4−CN−5−CHF2−PYR3]、[7574:1−Et−4−c−Pr−5−CHF2−PYR3]、[7575:1−Et−4−CHF2−5−CHF2−PYR3]、[7576:1−Et−4−CF3−5−CHF2−PYR3]、[7577:1−Et−5−CF3−PYR3]、[7578:1−Et−4−F−5−CF3−PYR3]、[7579:1−Et−4−Cl−5−CF3−PYR3]、[7580:1−Et−4−Br−5−CF3−PYR3]、[7581:1−Et−4−Me−5−CF3−PYR3]、[7582:1−Et−4−Et−5−CF3−PYR3]、[7583:1−Et−4−OMe−5−CF3−PYR3]、[7584:1−Et−4−OEt−5−CF3−PYR3]、[7585:1−Et−4−CN−5−CF3−PYR3]、[7586:1−Et−4−c−Pr−5−CF3−PYR3]、[7587:1−Et−4−CHF2−5−CF3−PYR3]、[7588:1−Et−4−CF3−5−CF3−PYR3]、[7589:1−Et−5−OPr−PYR3]、[7590:1−Et−4−F−5−OPr−PYR3]、[7591:1−Et−4−Cl−5−OPr−PYR3]、[7592:1−Et−4−Br−5−OPr−PYR3]、[7593:1−Et−4−Me−5−OPr−PYR3]、[7594:1−Et−4−Et−5−OPr−PYR3]、[7595:1−Et−4−OMe−5−OPr−PYR3]、[7596:1−Et−4−OEt−5−OPr−PYR3]、[7597:1−Et−4−CN−5−OPr−PYR3]、[7598:1−Et−4−c−Pr−5−OPr−PYR3]、[7599:1−Et−4−CHF2−5−OPr−PYR3]、[7600:1−Et−4−CF3−5−OPr−PYR3]、 [7501: 1-Et-4-CN-5-Me-PYR3], [7502: 1-Et-4-c-Pr-5-Me-PYR3], [7503: 1-Et-4-CHF2-5 -Me-PYR3], [7504: 1-Et-4-CF3-5-Me-PYR3], [7505: 1-Et-5-Et-PYR3], [7506: 1-Et-4-F-5 -Et-PYR3], [7507: 1-Et-4-Cl-5-Et-PYR3], [7508: 1-Et-4-Br-5-Et-PYR3], [7509: 1-Et-4 -Me-5-Et-PYR3], [7510: 1-Et-4-Et-5-Et-PYR3], [7511: 1-Et-4-OMe-5-Et-PYR3], [7512: 1 -Et-4-OEt-5-Et-PYR3], [7513: 1- t-4-CN-5-Et-PYR3], [7514: 1-Et-4-c-Pr-5-Et-PYR3], [7515: 1-Et-4-CHF2-5-Et-PYR3] [7516: 1-Et-4-CF3-5-Et-PYR3], [7517: 1-Et-5-OMe-PYR3], [7518: 1-Et-4-F-5-OMe-PYR3] [7519: 1-Et-4-Cl-5-OMe-PYR3], [7520: 1-Et-4-Br-5-OMe-PYR3], [7521: 1-Et-4-Me-5- OMe-PYR3], [7522: 1-Et-4-Et-5-OMe-PYR3], [7523: 1-Et-4-OMe-5-OMe-PYR3], [7524: 1-Et-4- OEt-5-OMe-PYR3], [7525: 1- t-4-CN-5-OMe-PYR3], [7526: 1-Et-4-c-Pr-5-OMe-PYR3], [7527: 1-Et-4-CHF2-5-OMe-PYR3] [7528: 1-Et-4-CF3-5-OMe-PYR3], [7529: 1-Et-5-OEt-PYR3], [7530: 1-Et-4-F-5-OEt-PYR3] [7531: 1-Et-4-Cl-5-OEt-PYR3], [7532: 1-Et-4-Br-5-OEt-PYR3], [7533: 1-Et-4-Me-5 OEt-PYR3], [7534: 1-Et-4-Et-5-OEt-PYR3], [7535: 1-Et-4-OMe-5-OEt-PYR3], [7536: 1-Et-4- OEt-5-OEt-PYR3], [7537 : 1-Et-4-CN-5-OEt-PYR3], [7538: 1-Et-4-c-Pr-5-OEt-PYR3], [7539: 1-Et-4-CHF2-5-OEt -PYR3], [7540: 1-Et-4-CF3-5-OEt-PYR3], [7541: 1-Et-5-CN-PYR3], [7542: 1-Et-4-F-5-CN -PYR3], [7543: 1-Et-4-Cl-5-CN-PYR3], [7544: 1-Et-4-Br-5-CN-PYR3], [7545: 1-Et-4-Me. -5-CN-PYR3], [7546: 1-Et-4-Et-5-CN-PYR3], [7547: 1-Et-4-OMe-5-CN-PYR3], [7548: 1-Et. -4-OEt-5-CN-PYR3], [7549: 1-E -4-CN-5-CN-PYR3], [7550: 1-Et-4-c-Pr-5-CN-PYR3], [7551: 1-Et-4-CHF2-5-CN-PYR3], [7552: 1-Et-4-CF3-5-CN-PYR3], [7553: 1-Et-5-c-Pr-PYR3], [7554: 1-Et-4-F-5-c-Pr -PYR3], [7555: 1-Et-4-Cl-5-c-Pr-PYR3], [7556: 1-Et-4-Br-5-c-Pr-PYR3], [7557: 1-Et. -4-Me-5-c-Pr-PYR3], [7558: 1-Et-4-Et-5-c-Pr-PYR3], [7559: 1-Et-4-OMe-5-c-Pr -PYR3], [7560: 1-Et-4-OEt-5-c-Pr-PYR3], [ 561: 1-Et-4-CN-5-c-Pr-PYR3], [7562: 1-Et-4-c-Pr-5-c-Pr-PYR3], [7563: 1-Et-4- CHF2-5-c-Pr-PYR3], [7564: 1-Et-4-CF3-5-c-Pr-PYR3], [7565: 1-Et-5-CHF2-PYR3], [7566: 1- Et-4-F-5-CHF2-PYR3], [7567: 1-Et-4-Cl-5-CHF2-PYR3], [7568: 1-Et-4-Br-5-CHF2-PYR3], [ 7569: 1-Et-4-Me-5-CHF2-PYR3], [7570: 1-Et-4-Et-5-CHF2-PYR3], [7571: 1-Et-4-OMe-5-CHF2- PYR3], [7572: 1-Et-4-OEt -5-CHF2-PYR3], [7573: 1-Et-4-CN-5-CHF2-PYR3], [7574: 1-Et-4-c-Pr-5-CHF2-PYR3], [7575: 1. -Et-4-CHF2-5-CHF2-PYR3], [7576: 1-Et-4-CF3-5-CHF2-PYR3], [7577: 1-Et-5-CF3-PYR3], [7578: 1 -Et-4-F-5-CF3-PYR3], [7579: 1-Et-4-Cl-5-CF3-PYR3], [7580: 1-Et-4-Br-5-CF3-PYR3], [7581: 1-Et-4-Me-5-CF3-PYR3], [7582: 1-Et-4-Et-5-CF3-PYR3], [7583: 1-Et-4-OMe-5-CF3 -PYR3], [7584: 1 Et-4-OEt-5-CF3-PYR3], [7585: 1-Et-4-CN-5-CF3-PYR3], [7586: 1-Et-4-c-Pr-5-CF3-PYR3] [7587: 1-Et-4-CHF2-5-CF3-PYR3], [7588: 1-Et-4-CF3-5-CF3-PYR3], [7589: 1-Et-5-OPr-PYR3] [7590: 1-Et-4-F-5-OPr-PYR3], [7591: 1-Et-4-Cl-5-OPr-PYR3], [7592: 1-Et-4-Br-5-5. OPr-PYR3], [7593: 1-Et-4-Me-5-OPr-PYR3], [7594: 1-Et-4-Et-5-OPr-PYR3], [7595: 1-Et-4- OMe-5-OPr-PYR3], [75 6: 1-Et-4-OEt-5-OPr-PYR3], [7597: 1-Et-4-CN-5-OPr-PYR3], [7598: 1-Et-4-c-Pr-5-5 OPr-PYR3], [7599: 1-Et-4-CHF2-5-OPr-PYR3], [7600: 1-Et-4-CF3-5-OPr-PYR3],
[7601:1−Et−5−OCH2CH=CH2−PYR3]、[7602:1−Et−4−F−5−OCH2CH=CH2−PYR3]、[7603:1−Et−4−Cl−5−OCH2CH=CH2−PYR3]、[7604:1−Et−4−Br−5−OCH2CH=CH2−PYR3]、[7605:1−Et−4−Me−5−OCH2CH=CH2−PYR3]、[7606:1−Et−4−Et−5−OCH2CH=CH2−PYR3]、[7607:1−Et−4−OMe−5−OCH2CH=CH2−PYR3]、[7608:1−Et−4−OEt−5−OCH2CH=CH2−PYR3]、[7609:1−Et−4−CN−5−OCH2CH=CH2−PYR3]、[7610:1−Et−4−c−Pr−5−OCH2CH=CH2−PYR3]、[7611:1−Et−4−CHF2−5−OCH2CH=CH2−PYR3]、[7612:1−Et−4−CF3−5−OCH2CH=CH2−PYR3]、[7613:1−Et−5−OCH2CH=CCl2−PYR3]、[7614:1−Et−4−F−5−OCH2CH=CCl2−PYR3]、[7615:1−Et−4−Cl−5−OCH2CH=CCl2−PYR3]、[7616:1−Et−4−Br−5−OCH2CH=CCl2−PYR3]、[7617:1−Et−4−Me−5−OCH2CH=CCl2−PYR3]、[7618:1−Et−4−Et−5−OCH2CH=CCl2−PYR3]、[7619:1−Et−4−OMe−5−OCH2CH=CCl2−PYR3]、[7620:1−Et−4−OEt−5−OCH2CH=CCl2−PYR3]、[7621:1−Et−4−CN−5−OCH2CH=CCl2−PYR3]、[7622:1−Et−4−c−Pr−5−OCH2CH=CCl2−PYR3]、[7623:1−Et−4−CHF2−5−OCH2CH=CCl2−PYR3]、[7624:1−Et−4−CF3−5−OCH2CH=CCl2−PYR3]、[7625:1−Et−5−OCH2C≡CH−PYR3]、[7626:1−Et−4−F−5−OCH2C≡CH−PYR3]、[7627:1−Et−4−Cl−5−OCH2C≡CH−PYR3]、[7628:1−Et−4−Br−5−OCH2C≡CH−PYR3]、[7629:1−Et−4−Me−5−OCH2C≡CH−PYR3]、[7630:1−Et−4−Et−5−OCH2C≡CH−PYR3]、[7631:1−Et−4−OMe−5−OCH2C≡CH−PYR3]、[7632:1−Et−4−OEt−5−OCH2C≡CH−PYR3]、[7633:1−Et−4−CN−5−OCH2C≡CH−PYR3]、[7634:1−Et−4−c−Pr−5−OCH2C≡CH−PYR3]、[7635:1−Et−4−CHF2−5−OCH2C≡CH−PYR3]、[7636:1−Et−4−CF3−5−OCH2C≡CH−PYR3]、[7637:1−Et−5−OCH2CF3−PYR3]、[7638:1−Et−4−F−5−OCH2CF3−PYR3]、[7639:1−Et−4−Cl−5−OCH2CF3−PYR3]、[7640:1−Et−4−Br−5−OCH2CF3−PYR3]、[7641:1−Et−4−Me−5−OCH2CF3−PYR3]、[7642:1−Et−4−Et−5−OCH2CF3−PYR3]、[7643:1−Et−4−OMe−5−OCH2CF3−PYR3]、[7644:1−Et−4−OEt−5−OCH2CF3−PYR3]、[7645:1−Et−4−CN−5−OCH2CF3−PYR3]、[7646:1−Et−4−c−Pr−5−OCH2CF3−PYR3]、[7647:1−Et−4−CHF2−5−OCH2CF3−PYR3]、[7648:1−Et−4−CF3−5−OCH2CF3−PYR3]、[7649:1−Et−5−CH2OCH3−PYR3]、[7650:1−Et−4−F−5−CH2OCH3−PYR3]、[7651:1−Et−4−Cl−5−CH2OCH3−PYR3]、[7652:1−Et−4−Br−5−CH2OCH3−PYR3]、[7653:1−Et−4−Me−5−CH2OCH3−PYR3]、[7654:1−Et−4−Et−5−CH2OCH3−PYR3]、[7655:1−Et−4−OMe−5−CH2OCH3−PYR3]、[7656:1−Et−4−OEt−5−CH2OCH3−PYR3]、[7657:1−Et−4−CN−5−CH2OCH3−PYR3]、[7658:1−Et−4−c−Pr−5−CH2OCH3−PYR3]、[7659:1−Et−4−CHF2−5−CH2OCH3−PYR3]、[7660:1−Et−4−CF3−5−CH2OCH3−PYR3] [7601: 1-Et-5-OCH2CH = CH2-PYR3], [7602: 1-Et-4-F-5-OCH2CH = CH2-PYR3], [7603: 1-Et-4-Cl-5-OCH2CH = CH2-PYR3], [7604: 1-Et-4-Br-5-OCH2CH = CH2-PYR3], [7605: 1-Et-4-Me-5-OCH2CH = CH2-PYR3], [7606: 1 -Et-4-Et-5-OCH2CH = CH2-PYR3], [7607: 1-Et-4-OMe-5-OCH2CH = CH2-PYR3], [7608: 1-Et-4-OEt-5-OCH2CH = CH2-PYR3], [7609: 1-Et-4-CN-5-OCH2CH = CH2-PYR3], [7610: 1-Et-4-c-Pr-5-OC. 2CH = CH2-PYR3], [7611: 1-Et-4-CHF2-5-OCH2CH = CH2-PYR3], [7612: 1-Et-4-CF3-5-OCH2CH = CH2-PYR3], [7613: 1-Et-5-OCH2CH = CCl2-PYR3], [7614: 1-Et-4-F-5-OCH2CH = CCl2-PYR3], [7615: 1-Et-4-Cl-5-OCH2CH = CCl2- PYR3], [7616: 1-Et-4-Br-5-OCH2CH = CCl2-PYR3], [7617: 1-Et-4-Me-5-OCH2CH = CCl2-PYR3], [7618: 1-Et- 4-Et-5-OCH2CH = CCl2-PYR3], [7619: 1-Et-4-OMe-5-OCH2CH = CCl2-PYR3 [7620: 1-Et-4-OEt-5-OCH2CH = CCl2-PYR3], [7621: 1-Et-4-CN-5-OCH2CH = CCl2-PYR3], [7622: 1-Et-4- c-Pr-5-OCH2CH = CCl2-PYR3], [7623: 1-Et-4-CHF2-5-OCH2CH = CCl2-PYR3], [7624: 1-Et-4-CF3-5-OCH2CH = CCl2- PYR3], [7625: 1-Et-5-OCH2C≡CH-PYR3], [7626: 1-Et-4-F-5-OCH2C≡CH-PYR3], [7627: 1-Et-4-Cl- 5-OCH2C≡CH-PYR3], [7628: 1-Et-4-Br-5-OCH2C≡CH-PYR3], [7629: 1-Et-4-Me-5-OC H2C≡CH-PYR3], [7630: 1-Et-4-Et-5-OCH2C≡CH-PYR3], [7631: 1-Et-4-OMe-5-OCH2C≡CH-PYR3], [7632: 1-Et-4-OEt-5-OCH2C≡CH-PYR3], [7633: 1-Et-4-CN-5-OCH2C≡CH-PYR3], [7634: 1-Et-4-c-Pr- 5-OCH2C≡CH-PYR3], [7635: 1-Et-4-CHF2-5-OCH2C≡CH-PYR3], [7636: 1-Et-4-CF3-5-OCH2C≡CH-PYR3], [7 7637: 1-Et-5-OCH2CF3-PYR3], [7638: 1-Et-4-F-5-OCH2CF3-PYR3], [7639: 1-Et-4-Cl-5-OCH2CF -PYR3], [7640: 1-Et-4-Br-5-OCH2CF3-PYR3], [7641: 1-Et-4-Me-5-OCH2CF3-PYR3], [7642: 1-Et-4-Et -5-OCH2CF3-PYR3], [7643: 1-Et-4-OMe-5-OCH2CF3-PYR3], [7644: 1-Et-4-OEt-5-OCH2CF3-PYR3], [7645: 1-Et -4-CN-5-OCH2CF3-PYR3], [7646: 1-Et-4-c-Pr-5-OCH2CF3-PYR3], [7647: 1-Et-4-CHF2-5-OCH2CF3-PYR3], [7648: 1-Et-4-CF3-5-OCH2CF3-PYR3], [7649: 1-Et-5-CH2OCH3-PYR3], [76 0: 1-Et-4-F-5-CH2OCH3-PYR3], [7651: 1-Et-4-Cl-5-CH2OCH3-PYR3], [7652: 1-Et-4-Br-5-CH2OCH3- PYR3], [7653: 1-Et-4-Me-5-CH2OCH3-PYR3], [7654: 1-Et-4-Et-5-CH2OCH3-PYR3], [7655: 1-Et-4-OMe- 5-CH2OCH3-PYR3], [7656: 1-Et-4-OEt-5-CH2OCH3-PYR3], [7657: 1-Et-4-CN-5-CH2OCH3-PYR3], [7658: 1-Et- 4-c-Pr-5-CH2OCH3-PYR3], [7659: 1-Et-4-CHF2-5-CH2OCH3-PYR3], [7660: 1-Et-4 -CF3-5-CH2OCH3-PYR3]
次に製剤例を示す。
製剤例1
本化合物Aのいずれか1化合物50部、リグニンスルホン酸カルシウム3部、ラウリル硫酸マグネシウム2部及び合成含水酸化珪素45部をよく粉砕混合することにより、製剤を得る。Next, formulation examples are shown.
Formulation Example 1
A preparation is obtained by thoroughly pulverizing and mixing 50 parts of any one of the present compounds A, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide.
製剤例2
本化合物Aのいずれか1化合物20部とソルビタントリオレエ−ト1.5部とを、ポリビニルアルコ−ル2部を含む水溶液28.5部と混合し、湿式粉砕法で微粉砕した後、この中に、キサンタンガム0.05部及びアルミニウムマグネシウムシリケ−ト0.1部を含む水溶液40部を加え、さらにプロピレングリコ−ル10部を加えて攪拌混合し、製剤を得る。Formulation Example 2
After mixing 20 parts of any one compound of this compound A and 1.5 parts of sorbitan trioleate with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, Into this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and stirred to obtain a preparation.
製剤例3
本化合物Aのいずれか1化合物2部、カオリンクレ−88部及びタルク10部をよく粉砕混合することにより、製剤を得る。Formulation Example 3
A formulation is obtained by thoroughly pulverizing and mixing 2 parts of any one compound of Compound A, 88 parts of kaolin clay and 10 parts of talc.
製剤例4
本化合物Aのいずれか1化合物5部、ポリオキシエチレンスチリルフェニルエ−テル14部、ドデシルベンゼンスルホン酸カルシウム6部及びキシレン75部をよく混合することにより、製剤を得る。Formulation Example 4
A preparation is obtained by thoroughly mixing 5 parts of any one of the present compounds A, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
製剤例5
本化合物Aのいずれか1化合物2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイト30部及びカオリンクレ−65部をよく粉砕混合した後、水を加えてよく練り合せ、造粒乾燥することにより、製剤を得る。Formulation Example 5
After thoroughly mixing 2 parts of any one compound A, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, water is added and kneaded and granulated. The preparation is obtained by drying.
製剤例6
本化合物Aのいずれか1化合物10部;ポリオキシエチレンアルキルエ−テルサルフェ−トアンモニウム塩50部を含むホワイトカ−ボン35部;及び水55部を混合し、湿式粉砕法で微粉砕することにより、製剤を得る。Formulation Example 6
By mixing 10 parts of any one compound of this compound A; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water, and finely pulverizing them by a wet pulverization method. Get the formulation.
次に、本発明化合物が有害生物の防除に有用であることを試験例で示す。
なお防除効果は、調査時の供試植物上の病斑の面積を目視観察し、本発明化合物を処理した植物の病斑の面積と、無処理の植物の病斑の面積とを比較することにより評価した。
試験例1
プラスチックポットに土壌を詰め、そこにイネ(品種;日本晴)を播種し、温室内で20日間生育させた。その後、本発明化合物11、13または16のいずれか一つの化合物を所定濃度(500ppm)含有するように調整した水希釈液を上記イネの葉面に充分付着するように茎葉散布した。散布後、植物を風乾し、昼間24℃、夜間20℃多湿下で、前記散布処理をしたイネと、イネいもち病菌(Magnaporthe grisea)に罹病したイネ苗(品種;日本晴)とを接触させながら6日間置いた後、病斑面積を調査した。その結果、本発明化合物11、13または16を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Next, test examples show that the compounds of the present invention are useful for pest control.
The control effect is to visually observe the area of the lesion on the test plant at the time of the survey, and to compare the area of the lesion on the plant treated with the compound of the present invention and the area of the lesion on the untreated plant. It was evaluated by.
Test example 1
A plastic pot was filled with soil, rice (cultivar; Nipponbare) was sown therein, and grown in a greenhouse for 20 days. Thereafter, a dilute water adjusted to contain any one of the compounds 11, 13 or 16 of the present invention so as to contain a predetermined concentration (500 ppm) was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the rice. After spraying, the plants were air-dried, and the sprayed rice was contacted with rice seedlings (variety: Nihonbare) affected by rice blast fungus (Magnaporthe grisea) under high humidity at 24 ° C in the daytime and 20 ° C at night. After leaving for days, the lesion area was examined. As a result, the lesion area in the plant treated with the compound 11, 13 or 16 of the present invention was 30% or less of the lesion area in the untreated plant.
試験例2
プラスチックポットに土壌を詰め、そこにイネ(品種;日本晴)を播種し、温室内で20日間生育させた。その後、本発明化合物1、10または15のいずれか一つの化合物をを所定濃度(200ppm)含有するように調整した水希釈液を、上記イネの葉面に充分付着するように茎葉散布した。散布後、植物を風乾し、昼間24℃、夜間20℃多湿下で、前記散布処理をしたイネと、イネいもち病菌(Magnaporthe grisea)に罹病したイネ苗(品種;日本晴)とを接触させながら6日間置いた後、病斑面積を調査した。その結果、本発明化合物1、10または15を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test example 2
A plastic pot was filled with soil, rice (cultivar; Nipponbare) was sown therein, and grown in a greenhouse for 20 days. Thereafter, a dilute water prepared by containing any one of the compounds 1, 10 or 15 of the present invention so as to contain a predetermined concentration (200 ppm) was sprayed on the foliage so as to sufficiently adhere to the leaf surface of the rice. After spraying, the plants were air-dried, and the sprayed rice was contacted with rice seedlings (variety: Nihonbare) affected by rice blast fungus (Magnaporthe grisea) under high humidity at 24 ° C in the daytime and 20 ° C at night. After leaving for days, the lesion area was examined. As a result, the lesion area in the plant treated with the present compound 1, 10 or 15 was 30% or less of the lesion area in the untreated plant.
試験例3
プラスチックポットに土壌を詰め、そこにオオムギ(品種;ニシノホシ)を播種し、温室で7日間生育させた。本発明化合物1または3〜16のいずれか一つの化合物を所定濃度(500ppm)含有するように調整した水希釈液を、上記オオムギの葉面に充分付着するように茎葉散布した。散布後植物を風乾し、2日後にオオムギ網斑病菌(Pyrenophora teres)胞子の水懸濁液を噴霧接種した。接種後植物を昼間23℃、夜間20℃の温室内で多湿下に3日間置き、次に温室内で7日間栽培した後、病斑面積を調査した。その結果、本発明化合物1または3〜16を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test example 3
A plastic pot was filled with soil, and barley (variety: Nishinohoshi) was sown therein and grown in a greenhouse for 7 days. A water dilution adjusted to contain a predetermined concentration (500 ppm) of any one of the compounds 1 or 3 to 16 of the present invention was sprayed on the foliage so as to adhere well to the leaf surface of the barley. After spraying, the plants were air-dried, and two days later, an aqueous suspension of barley net spore fungus (Pyrenophora teres) spores was spray-inoculated. After inoculation, the plants were placed under high humidity in a greenhouse at 23 ° C. during the day and 20 ° C. during the night, and then cultivated in the greenhouse for 7 days. As a result, the lesion area in the plant treated with the present compound 1 or 3 to 16 was 30% or less of the lesion area in the untreated plant.
試験例4
プラスチックポットに土壌を詰め、インゲン(品種;長鶉菜豆)を播種し、温室内で8日間生育させた。本発明化合物4または6のいずれか一つの化合物を所定濃度(500ppm)含有するように調整した水希釈液を、上記インゲン葉面に充分付着するように茎葉散布した。散布後植物を風乾し、インゲン菌核病菌(Sclerotinia sclerotiorum)の菌糸含有PDA培地をインゲン葉面上に置いた。接種後全てのインゲンは夜間のみ多湿下におき、接種4日後に病斑面積を調査した。その結果、本発明化合物4または6を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test example 4
A plastic pot was stuffed with soil, seeded with green beans (variety; Nagahama peas) and grown in a greenhouse for 8 days. A dilute water adjusted to contain any one of the compounds 4 or 6 of the present invention so as to contain a predetermined concentration (500 ppm) was sprayed on the foliage so that it sufficiently adheres to the kidney leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of sclerotia sclerotium was placed on the kidney leaf surface. After the inoculation, all kidney beans were placed under high humidity only at night, and the lesion area was examined 4 days after the inoculation. As a result, the lesion area in the plant treated with the compound 4 or 6 of the present invention was 30% or less of the lesion area in the untreated plant.
試験例5
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジ−)を播種し、温室内で10日間生育させた。本発明化合物1〜8または10〜16のいずれか一つの化合物を所定濃度(500ppm)含有するように調整した水希釈液を、上記コムギの葉面に充分付着するように茎葉散布した。散布後植物を風乾し、4日後にコムギ葉枯病菌(Septoria tritici)胞子の水懸濁液を噴霧接種した。接種後植物を18℃多湿下に3日間置き、次に照明下に14日から18日間置いた後、病斑面積を調査した。その結果、本発明化合物1〜8または10〜16を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test Example 5
A plastic pot was filled with soil, and wheat (variety: Apogee) was sown therein and grown in a greenhouse for 10 days. The water dilution adjusted to contain any one of the compounds 1 to 8 or 10 to 16 of the present invention in a predetermined concentration (500 ppm) was sprayed on the foliage so as to adhere sufficiently to the leaf surface of the wheat. After spraying, the plants were air-dried, and after 4 days, sprayed with a water suspension of Septoria tritici spores. After inoculation, the plants were placed under high humidity at 18 ° C. for 3 days, then placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 1-8 or 10-16 was 30% or less of the lesion area in the untreated plant.
試験例6
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジ−)を播種し、温室内で10日間生育させた。その後、該コムギにコムギ葉枯病菌(Septoria tritici)胞子の水懸濁液を噴霧接種した。該コムギを18℃、多湿下に3日間置いた後、風乾した。本発明化合物1、7、8、12または14〜16のいずれか一つの化合物を所定濃度(200ppm)含有するように調整した水希釈液を、上記コムギの葉面に充分付着するように茎葉散布した。散布後植物を風乾し、さらに照明下に14日から18日間置いた後、病斑面積を調査した。その結果、本発明化合物1、7、8、12または14〜16を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test Example 6
A plastic pot was filled with soil, and wheat (variety: Apogee) was sown therein and grown in a greenhouse for 10 days. Thereafter, the wheat was spray-inoculated with an aqueous suspension of Septoria tritici spores. The wheat was placed under high humidity at 18 ° C. for 3 days and then air-dried. Dispersion of the water dilution adjusted to contain a predetermined concentration (200 ppm) of any one of the compounds 1, 7, 8, 12 or 14 to 16 of the present invention so as to adhere sufficiently to the leaf surface of the wheat. did. After spraying, the plants were air-dried and placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the present compound 1, 7, 8, 12 or 14 to 16 was 30% or less of the lesion area in the untreated plant.
試験例7
プラスチックポットに土壌を詰め、そこにコムギ(品種;アポジ−)を播種し、温室内で10日間生育させた。その後、該コムギにコムギ葉枯病菌(Septoria tritici)胞子の水懸濁液を噴霧接種した。該コムギを18℃、多湿下に3日間置いた後、風乾した。本発明化合物3を所定濃度(50ppm)含有するように調整した水希釈液を、上記コムギの葉面に充分付着するように茎葉散布した。散布後植物を風乾し、さらに照明下に14日から18日間置いた後、病斑面積を調査した。その結果、本発明化合物3を処理した植物における病斑面積は、無処理の植物における病斑面積の30%以下であった。Test Example 7
A plastic pot was filled with soil, and wheat (variety: Apogee) was sown therein and grown in a greenhouse for 10 days. Thereafter, the wheat was spray-inoculated with an aqueous suspension of Septoria tritici spores. The wheat was placed under high humidity at 18 ° C. for 3 days and then air-dried. A dilute water adjusted to contain a predetermined concentration (50 ppm) of the compound 3 of the present invention was sprayed on the foliage so as to adhere sufficiently to the leaf surface of the wheat. After spraying, the plants were air-dried and placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compound 3 of the present invention was 30% or less of the lesion area in the untreated plant.
試験例8
プラスチックポットに土壌を詰め、そこにコムギ(品種;シロガネ)を播種し、温室内で9日間生育させた。本発明化合物12または14〜16のいずれか一つの化合物を所定濃度(200ppm)含有するように調整した水希釈液を、上記コムギの葉面に充分付着するように茎葉散布した。散布後植物を風乾し、20℃、照明下で5日間栽培した後、コムギのさび病菌(Puccinia recondita)の胞子をふりかけ接種した。接種後植物を23℃、暗黒多湿下に1日間置いた後、20℃、照明下で8日間栽培し、病斑面積を調査した。その結果、本発明化合物12または14〜16を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test Example 8
A plastic pot was filled with soil, and wheat (variety: Shirogane) was sown therein and allowed to grow in a greenhouse for 9 days. A water dilution adjusted to contain a predetermined concentration (200 ppm) of any one of the compounds 12 or 14 to 16 of the present invention was sprayed on the foliage so as to adhere well to the leaf surface of the wheat. After spraying, the plants were air-dried and cultivated at 20 ° C. under illumination for 5 days, and then sprinkled with spores of wheat rust fungus (Puccinia recondita). After inoculation, the plants were placed at 23 ° C. under dark and humid conditions for 1 day, then cultivated at 20 ° C. under illumination for 8 days, and the lesion area was examined. As a result, the lesion area in the plant treated with the present compound 12 or 14 to 16 was 30% or less of the lesion area in the untreated plant.
試験例9
プラスチックポットに土壌を詰め、そこにオオムギ(品種;ミカモゴールデン)を播種し、温室で7日間生育させた。本発明化合物14、15または16のいずれか一つの化合物を所定濃度(200ppm)含有するように調整した水希釈液を、上記オオムギの葉面に充分付着するように茎葉散布した。散布後植物を風乾し、2日後にオオムギ雲形病菌(Rhynchosporium secalis)胞子の水懸濁液を噴霧接種した。接種後植物を昼間23℃、夜間20℃の温室内で多湿下に3日間置き、次に温室内で7日間栽培した後、病斑面積を調査した。その結果、本発明化合物14、15または16を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test Example 9
A plastic pot was filled with soil, and barley (variety: Mikamo Golden) was sown there and allowed to grow in a greenhouse for 7 days. A water dilution adjusted to contain a predetermined concentration (200 ppm) of any one of the compounds 14, 15 or 16 of the present invention was sprayed on the foliage so as to adhere well to the leaf surface of the barley. After spraying, the plants were air-dried, and after 2 days, sprayed with a water suspension of barley cloud spore (Rhynchosporium secalis) spores. After inoculation, the plants were placed under high humidity in a greenhouse at 23 ° C. during the day and 20 ° C. during the night, and then cultivated in the greenhouse for 7 days. As a result, the lesion area in the plant treated with the compound 14, 15 or 16 of the present invention was 30% or less of the lesion area in the untreated plant.
試験例10
プラスチックポットに土壌を詰め、そこにキュウリ(品種;相模半白)を播種し、温室内で12日間生育させた。本発明化合物3〜5、12、14または16のいずれか一つの化合物を所定濃度(500ppm)含有するように調整した水希釈液を、上記キュウリ葉面に充分付着するように茎葉散布した。散布後植物を風乾し、キュウリうどんこ病菌(Sphaerotheca fuliginea)胞子をふりかけ接種した。植物を昼間24℃、夜間20℃の温室で8日間栽培した後、病斑面積を調査した。その結果、本発明化合物3〜5、12、14または16を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test Example 10
A plastic pot was filled with soil, and cucumber (variety: Sagamihanjiro) was sown there and allowed to grow in a greenhouse for 12 days. A water dilution adjusted to contain any one of the compounds of the present invention compounds 3-5, 12, 14 or 16 at a predetermined concentration (500 ppm) was sprayed on the foliage so that it sufficiently adhered to the cucumber leaf surface. After spraying, the plants were air-dried and sprinkled with spore powdery mildew (Sphaerotheca furiginea) spores. The plants were cultivated in a greenhouse at 24 ° C. during the day and 20 ° C. during the night for 8 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 3-5, 12, 14, or 16 was 30% or less of the lesion area in the untreated plant.
試験例11
プラスチックポットに土壌を詰め、そこにキュウリ(品種;相模半白)を播種し、温室内で19日間生育させた。本発明化合物6を所定濃度(200ppm)含有するように調整した水希釈液を、上記キュウリ葉面に充分付着するように茎葉散布した。散布後植物を風乾し、1日後にキュウリ褐斑病菌(Corynespora cassiicola)胞子の水懸濁液を噴霧接種した。接種後は昼間24℃、夜間20℃の多湿下で7日間栽培した後、病斑面積を調査した。その結果、本発明化合物6を処理した植物における病斑面積は、無処理の植物における病斑面積の30%以下であった。Test Example 11
A plastic pot was filled with soil, and cucumber (variety: Sagamihanjiro) was sown there and allowed to grow in a greenhouse for 19 days. A dilute water adjusted to contain the present compound 6 at a predetermined concentration (200 ppm) was sprayed on the foliage so as to adhere sufficiently to the cucumber leaf surface. After spraying, the plants were air-dried, and one day later, sprayed and inoculated with a water suspension of cucumber brown spot fungus (Corynespora cassicola) spores. After inoculation, the plants were cultivated for 7 days under high humidity at 24 ° C in the daytime and 20 ° C at night, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compound 6 of the present invention was 30% or less of the lesion area in the untreated plant.
試験例12
プラスチックポットに土壌を詰め、そこにキュウリ(品種;相模半白)を播種し、温室内で19日間生育させた。本発明化合物11〜13、15または16をのいずれか一つの化合物を所定濃度(200ppm)含有するように調整した水希釈液を、上記キュウリ葉面に充分付着するように茎葉散布した。散布後植物を風乾し、1日後にキュウリ炭そ病菌(Colletotrichum lagenarium)胞子の水懸濁液を噴霧接種した。接種後はじめは23℃、多湿下に1日間置き、続いて昼間24℃、夜間20℃の温室で6日間栽培した後、病斑面積を調査した。その結果、本発明化合物11〜13、15または16を処理した植物における病斑面積はいずれも、無処理の植物における病斑面積の30%以下であった。Test Example 12
A plastic pot was filled with soil, and cucumber (variety: Sagamihanjiro) was sown there and allowed to grow in a greenhouse for 19 days. A water dilution adjusted to contain any one of the present compounds 11 to 13, 15 or 16 at a predetermined concentration (200 ppm) was sprayed on the foliage so that it sufficiently adhered to the cucumber leaf surface. After spraying, the plants were air-dried, and one day later, sprayed and inoculated with an aqueous suspension of cucumber anthracnose fungus (Colletotrichum lagenarium) spores. After inoculation, it was first placed at 23 ° C. under high humidity for 1 day, and then cultivated in a greenhouse at 24 ° C. during the day and 20 ° C. during the night, and then the lesion area was examined. As a result, the lesion area in the plant treated with the present compounds 11 to 13, 15 or 16 was 30% or less of the lesion area in the untreated plant.
試験例13
本発明化合物9を有効成分濃度が500ppmとなるように水で希釈し、試験用薬液を調製した。
直径5.5cmのポリエチレンカップの底に同大の濾紙を敷き、上記試験用薬液0.7mlを濾紙上に滴下し、餌としてショ糖30mgを均一に入れた。該ポリエチレンカップ内にイエバエ(Musca domestica)雌成虫10頭を放ち、蓋をした。24時間後にイエバエの生死を調査し、次式により死虫率を求めた。
死虫率(%)=(死亡虫数/供試虫数)×100
その結果、本発明化合物9の処理においては死虫率100%を示した。Test Example 13
The compound 9 of the present invention was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
A filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as food. Ten female fly (Musca domestica) females were released into the polyethylene cup and capped. The life and death of the housefly was investigated 24 hours later, and the mortality rate was calculated by the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100
As a result, the treatment with Compound 9 of the present invention showed a mortality rate of 100%.
試験例14
本発明化合物12または14を有効成分濃度が500ppmとなるように水で希釈し、試験用薬液を調製した。
ポリエチレンカップにキャベツ(品種;グリーンボール)を植え、第3本葉ないしは第4本葉が展開するまで生育させた。そのキャベツに上記の試験用薬液を20mL/カップの割合で散布した。薬液が乾いた後、ろ紙を敷いた直径5.5cmのポリエチレンカップに根元から切り取ったキャベツを設置し、コナガ(Plutella xylostella)3令幼虫5頭を放ち、蓋をした。25℃で保管し、5日後に生存虫数を数え、次式より死虫率を求めた。
死虫率(%)=(死亡虫数/供試虫数)×100
その結果、本発明化合物12または14の試験用薬液の処理区は死虫率80%以上を示した。Test Example 14
The compound of the present invention 12 or 14 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test chemical solution.
Cabbage (variety: green ball) was planted in a polyethylene cup and allowed to grow until the third or fourth true leaf developed. The test chemical was sprayed on the cabbage at a rate of 20 mL / cup. After the chemical solution was dried, cabbage cut out from the root was placed in a polyethylene cup with a diameter of 5.5 cm covered with filter paper, and 5 third-instar larvae (Plutella xylostella) were released and capped. After storing at 25 ° C., the number of live insects was counted after 5 days, and the death rate was calculated from the following formula.
Death rate (%) = (Number of dead insects / number of test insects) × 100
As a result, the treatment group of the test chemical solution of the present compound 12 or 14 showed a death rate of 80% or more.
試験例15
本発明化合物12を有効成分濃度が500ppmとなるように水で希釈し、試験用薬液を調製した。
ポリエチレンカップで第1本葉が展開するまで育成したキュウリ(品種;相模半白節成)葉上に、ワタアブラムシ(Aphis gossypii)30頭(成虫、幼虫を含む)を放し、翌日上記試験用薬液20mLを散布した。6日後に生存虫数を数え、次式により防除価を求めた。
防除価(%)={1−(Cb×Tai)/(Cai×Tb)}×100
なお、式中の文字は以下の意味を表す。
Cb:無処理区の薬液散布前の虫数
Cai:無処理区の生存虫数
Tb:処理区の薬液散布前の虫数
Tai:処理区の生存虫数
その結果、本発明化合物12は、防除価90%以上を示した。Test Example 15
The compound 12 of the present invention was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test chemical solution.
30 cotton aphids (including adults and larvae) were released on the cucumber (variety: Sagamihanshirabushi adult) grown until the first true leaf developed in a polyethylene cup, and the above test solution was used the next day. 20 mL was sprayed. Six days later, the number of surviving insects was counted, and the control value was determined by the following formula.
Control value (%) = {1− (Cb × Tai) / (Cai × Tb)} × 100
In addition, the character in a formula represents the following meaning.
Cb: Number of insects before spraying chemical solution in untreated group Cai: Number of live insects in untreated group Tb: Number of insects before spraying chemical solution in treated group Tai: Number of live insects in treated group As a result, the present compound 12 was controlled The value was 90% or more.
Claims (6)
〔式中、
R5は、1以上のハロゲン原子を有していてもよいC1−C3アルキル基を表し;
Eは2価の5員ヘテロアリール基または2価の6員ヘテロアリール基を表し;
Yは、*−(CH2)n−G−&、*−G−(CH2)n−&、*−G−(CH2)n−G−&、*−G−CH2CH2−G−CH2CH2−G−&、*−CH2−G−CH2CH2−G−&、*−G−CH2CH2−G−CH2−&、*−CH=CH−&、*−CH=CH−G−&、*−G−CH=CH−&、*−CH=CH−CH2−G−&、*−G−CH2−CH=CH−&、*−G−CH=CH−CH2−&、*−CH2−CH=CH−G−&、*−CH=CH−G−CH2−&、*−CH2−G−CH=CH−&、*−CH=CH−CH2−G−CH2−&、*−CH2−G−CH2−CH=CH−&、*−CH=CH−G−CH2CH2−&、*−CH2CH2−G−CH=CH−&、*−G−CH=CH−CH2CH2−&、*−CH2CH2−CH=CH−G−&、*−CH=CH−G−CH=CH−&、*−C≡C−&、*−C≡C−CH2−G−&、*−G−CH2−C≡C−&、*−C≡C−CH2−G−CH2−&または*−CH2−G−CH2−C≡C−&を表し
(但し、Yの有する全ての水素原子は(Gが有する水素原子も含む)、ハロゲン原子およびC1−C3アルキル基からなる群より選ばれる1以上の原子または基で置換されていてもよく、2以上の原子または基で置換される場合、該原子および基は同一または相異なっていてもよく;Gは酸素原子、硫黄原子、またはNRBを表し;RBは、水素原子またはC1−C3アルキル基を表し、nは1〜10の整数を表す。また、Yにおいて、*はQとの結合位置を表し、&はEとの結合位置を表す。);
Qは、2価のC6−C10アリール基(但し、該2価のC6−C10アリール基は、群P2から選ばれる1以上の原子または基を有していてもよい。)または2価の5−10員ヘテロ環基(但し、該2価の5−10員ヘテロ環基は、群P2から選ばれる1以上の原子もしくは基を有していてもよく、環構成原子として窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を含有し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよい。)を表し;
Xは、酸素原子または硫黄原子を表し;
Aは、C6−C10アリール基、アダマンチル基、C6−C10アリールオキシ基、C6−C10アリールチオ基、C6−C10アリールアミノ基、C3−C10シクロアルキル基、5−10員ヘテロ環基、5−10員ヘテロアリールオキシ基、5−10員ヘテロアリールチオ基、5−10員ヘテロアリールアミノ基、C6−C10アリールスルホニル基、C6−C10アリールスルフィニル基、または群P3から選ばれる1もしくは2の基を有していてもよい−CH=NHを表す(但し、該5−10員ヘテロ環基、該5−10員ヘテロアリールオキシ基、該5−10員ヘテロアリールチオ基および該5−10員ヘテロアリールアミノ基は、環構成原子として窒素原子、酸素原子および硫黄原子からなる群より選ばれる1以上の原子を含有し、2以上の原子を含有する場合、該原子は同一もしくは相異なっていてもよく、また、該5−10員ヘテロ環基、該5−10員ヘテロアリールオキシ基、5−10員ヘテロアリールチオ基および5−10員ヘテロアリールアミノ基は、群P1から選ばれる1以上の原子もしくは基を有していてもよく、2以上の原子もしくは基を有する場合、該原子もしくは基は同一または相異なっていてもよく、
該−CH=NHが群P3から選ばれる基を2つ有する場合、該基は同一または相異なっていてもよく、
該C6−C10アリール基、該アダマンチル基、該C6−C10アリールオキシ基、該C6−C10アリールチオ基、該C6−C10アリールアミノ基、該C3−C10シクロアルキル基、該C6−C10アリールスルホニル基および該C6−C10アリールスルフィニル基は、群P1から選ばれる1以上の原子もしくは基を有していてもよく、2以上の原子もしくは基を有する場合、該原子もしくは基は同一または相異なっていてもよい。)。
群P1:ハロゲン原子、C1−C6アルキル基、C1−C6ハロアルキル基、C2−C6アルケニル基、C2−C6ハロアルケニル基、C2−C6アルキニル基、C2−C6ハロアルキニル基、C3−C6シクロアルキル基、C3−C6ハロシクロアルキル基、C1−C6アルコキシ基、C1−C6ハロアルコキシ基、C1−C6アルキルチオ基、C1−C6ハロアルキルチオ基、C3−C6シクロアルキルオキシ基、C3−C6ハロシクロアルキルオキシ基、C3−C6シクロアルキルチオ基、C3−C6アルケニルオキシ基、C3−C6アルキニルオキシ基、C3−C6ハロアルケニルオキシ基、C3−C6ハロアルキニルオキシ基、C3−C6アルケニルチオ基、C3−C6アルキニルチオ基、C3−C6ハロアルケニルチオ基、C3−C6ハロアルキニルチオ基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C6アルキルカルボニルオキシ基、C2−C6アルキルカルボニルチオ基、カルボキシ基、ホルミル基、C2−C6アルコキシカルボニル基、ニトロ基、シアノ基、ヒドロキシ基、C1−C6アルキルスルホニル基、C1−C6ハロアルキルスルホニル基、、C1−C6アルキルスルフィニル基、C1−C6ハロアルキルスルフィニル基、C1−C6アルキル基を有していてもよいアミノ基、C1−C6アルキル基を有していてもよいアミノスルホニル基およびC1−C6アルキル基を有していてもよいアミノカルボニル基からなる群;
群P2:ハロゲン原子、シアノ基、C3−C6シクロアルキル基、C3−C6ハロシクロアルキル基、C1−C4アルコキシ基、C1−C4ハロアルコキシ基、C1−C4アルキルチオ基およびC1−C4ハロアルキルチオ基からなる群;
群P3:C1−C6アルキル基、C1−C6ハロアルキル基、C3−C6シクロアルキル基、およびC3−C6ハロシクロアルキル基からなる群;〕
で示されるテトラゾリノン化合物。Formula (1)
[Where,
R 5 represents a C1-C3 alkyl group optionally having one or more halogen atoms;
E represents a divalent 5-membered heteroaryl group or a divalent 6-membered heteroaryl group;
Y is, * - (CH 2) n -G - &, * - G- (CH 2) n - &, * - G- (CH 2) n -G - &, * - G-CH 2 CH 2 - G-CH 2 CH 2 -G - &, * - CH 2 -G-CH 2 CH 2 -G - &, * - G-CH 2 CH 2 -G-CH 2 - &, * - CH = CH- & , * - CH = CH-G - &, * - G-CH = CH - &, * - CH = CH-CH 2 -G - &, * - G-CH 2 -CH = CH - &, * - G -CH = CH-CH 2 - & , * - CH 2 -CH = CH-G - &, * - CH = CH-G-CH 2 - &, * - CH 2 -G-CH = CH - &, * -CH = CH-CH 2 -G- CH 2 - &, * - CH 2 -G-CH 2 -CH = CH - &, * - CH = CH-G-CH 2 CH 2 - &, * - CH 2 CH 2 -G-CH = CH- & * -G-CH = CH-CH 2 CH 2 - &, * - CH 2 CH 2 -CH = CH-G - &, * - CH = CH-G-CH = CH - &, * - C≡C- &, * - C≡C-CH 2 -G - &, * - G-CH 2 -C≡C - &, * - C≡C-CH 2 -G-CH 2 - & or * -CH 2 -G —CH 2 —C≡C— & (wherein all hydrogen atoms in Y (including hydrogen atoms in G) are one or more atoms selected from the group consisting of halogen atoms and C1-C3 alkyl groups) Or when substituted with two or more atoms or groups, the atoms and groups may be the same or different; G represents an oxygen atom, a sulfur atom, or NR B ; R B represents a hydrogen atom or a C1-C3 alkyl group, n represents an integer from 1 to 10. Furthermore, our in Y Te, * represents the bonding position with Q, & represents a bonding position to E).;
Q is a divalent C6-C10 aryl group (provided that the bivalent C6-C10 aryl group may have one or more atoms or groups selected from the group P 2.) Or divalent 5-10-membered heterocyclic group (provided that the divalent 5-10-membered heterocyclic group may have one or more atoms or groups selected from group P 2 , and a nitrogen atom as a ring-constituting atom, 1 or more atoms selected from the group consisting of an oxygen atom and a sulfur atom are contained, and when 2 or more atoms are contained, these atoms may be the same or different.
X represents an oxygen atom or a sulfur atom;
A represents a C6-C10 aryl group, an adamantyl group, a C6-C10 aryloxy group, a C6-C10 arylthio group, a C6-C10 arylamino group, a C3-C10 cycloalkyl group, a 5-10 membered heterocyclic group, 5-10 membered heteroaryl group, 5-10-membered heteroarylthio group, 5-10 membered heteroaryl amino group, C6-C10 arylsulfonyl group, C6-C10 arylsulfinyl group or 1 or 2 groups selected from the group P 3, -CH = NH which may have (provided that the 5-10 membered heterocyclic group, the 5-10 membered heteroaryloxy group, the 5-10 membered heteroarylthio group and the 5-10 member The heteroarylamino group contains one or more atoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring constituent atoms. When two or more atoms are contained, the atoms may be the same or different, and the 5-10 membered heterocyclic group, the 5-10 membered heteroaryloxy group, the 5-10 membered heteroarylthio group groups and 5-10 membered heteroaryl amino group may have one or more atoms or groups selected from the group P 1, if having two or more atoms or groups, the atom or group are the same or different May be different,
When the —CH═NH has two groups selected from the group P 3 , the groups may be the same or different;
The C6-C10 aryl group, the adamantyl group, the C6-C10 aryloxy group, the C6-C10 arylthio group, the C6-C10 arylamino group, the C3-C10 cycloalkyl group, the C6-C10 arylsulfonyl group and the C6-C10 arylsulfinyl group may have one or more atoms or groups selected from the group P 1, if having two or more atoms or groups, the atom or group are identical or different Also good. ).
Group P 1 : halogen atom, C1-C6 alkyl group, C1-C6 haloalkyl group, C2-C6 alkenyl group, C2-C6 haloalkenyl group, C2-C6 alkynyl group, C2-C6 haloalkynyl group, C3-C6 cycloalkyl Group, C3-C6 halocycloalkyl group, C1-C6 alkoxy group, C1-C6 haloalkoxy group, C1-C6 alkylthio group, C1-C6 haloalkylthio group, C3-C6 cycloalkyloxy group, C3-C6 halocycloalkyl group Oxy group, C3-C6 cycloalkylthio group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C3-C6 haloalkenyloxy group, C3-C6 haloalkynyloxy group, C3-C6 alkenylthio group, C3-C6 Alkynylthio group, C3-C6 haloalkenylthio group, C -C6 haloalkynylthio group, C2-C6 alkylcarbonyl group, C2-C6 haloalkylcarbonyl group, C2-C6 alkylcarbonyloxy group, C2-C6 alkylcarbonylthio group, carboxy group, formyl group, C2-C6 alkoxycarbonyl group, It may have a nitro group, a cyano group, a hydroxy group, a C1-C6 alkylsulfonyl group, a C1-C6 haloalkylsulfonyl group, a C1-C6 alkylsulfinyl group, a C1-C6 haloalkylsulfinyl group, or a C1-C6 alkyl group. A group consisting of an amino group, an aminosulfonyl group optionally having a C1-C6 alkyl group, and an aminocarbonyl group optionally having a C1-C6 alkyl group;
Group P 2 : halogen atom, cyano group, C3-C6 cycloalkyl group, C3-C6 halocycloalkyl group, C1-C4 alkoxy group, C1-C4 haloalkoxy group, C1-C4 alkylthio group and C1-C4 haloalkylthio group A group consisting of:
Group P 3 : a group consisting of a C1-C6 alkyl group, a C1-C6 haloalkyl group, a C3-C6 cycloalkyl group, and a C3-C6 halocycloalkyl group;
A tetrazolinone compound represented by:
群P4:E1〜E7からなる群
〔式中、#はテトラゾリノン環との結合位置を表し、$はYとの結合位置を表す。また、Z1は、窒素原子またはCR1を表し;
Z2は、窒素原子またはCR2を表し;
Z3は、窒素原子またはCR3を表し;
Z4は、窒素原子またはCR4を表し;
Y1は、酸素原子、硫黄原子またはNR8を表し;
Y2は、酸素原子、硫黄原子またはNR6を表し;
Y3は、酸素原子、硫黄原子またはNR7を表し;
R1は、水素原子、C1−C6アルキル基、C3−C6シクロアルキル基、ハロゲン原子、C1−C6ハロアルキル基、C2−C6アルケニル基、C1−C6アルコキシ基、C1−C6アルキルチオ基、C2−C6アルキニル基、ニトロ基、シアノ基、C1−C6アルキル基を有していてもよいアミノカルボニル基、C2−C6ハロアルケニル基、C2−C6ハロアルキニル基、C3−C6ハロシクロアルキル基、C1−C6ハロアルコキシ基、C1−C6ハロアルキルチオ基、C3−C6シクロアルキルオキシ基、C3−C6ハロシクロアルキルオキシ基、C3−C6シクロアルキルチオ基、C3−C6アルケニルオキシ基、C3−C6アルキニルオキシ基、C3−C6ハロアルケニルオキシ基、C3−C6ハロアルキニルオキシ基、C3−C6アルケニルチオ基、C3−C6アルキニルチオ基、C3−C6ハロアルケニルチオ基、C3−C6ハロアルキニルチオ基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C6アルキルカルボニルオキシ基、C2−C6アルキルカルボニルチオ基、C2−C6アルコキシカルボニル基、ヒドロキシ基、チオール基、C1−C6アルキル基を有していてもよいアミノ基、ペンタフルオロスルファニル基、C3−C9トリアルキルシリル基、C5−C14トリアルキルシリルエチニル基、C1−C4アルキルスルホニル基、C1−C4ハロアルキルスルホニル基、C1−C4アルキルスルフィニル基、C1−C4ハロアルキルスルフィニル基、C2−C5アルコキシアルキル基またはC2−C5アルキルチオアルキル基を表し;
R2,R3およびR4はそれぞれ独立して、水素原子、ハロゲン原子、C1−C3アルキル基、C1−C3ハロアルキル基、C2−C3アルケニル基、C2−C3ハロアルケニル基またはC1−C3アルコキシ基を表し;
R6およびR7はそれぞれ独立して、水素原子、C1−C3アルキル基、C1−C3ハロアルキル基、C2−C3アルケニル基、C2−C3ハロアルケニル基またはC1−C3アルコキシ基を表し;
R8は、水素原子、C1−C6アルキル基、C3−C6シクロアルキル基、C1−C6ハロアルキル基、C2−C6アルケニル基、C1−C6アルコキシ基、C1−C6アルキルチオ基、C2−C6アルキニル基、ニトロ基、シアノ基、C1−C6アルキル基を有していてもよいアミノカルボニル基、C2−C6ハロアルケニル基、C2−C6ハロアルキニル基、C3−C6ハロシクロアルキル基、C1−C6ハロアルコキシ基、C1−C6ハロアルキルチオ基、C3−C6シクロアルキルオキシ基、C3−C6ハロシクロアルキルオキシ基、C3−C6シクロアルキルチオ基、C3−C6アルケニルオキシ基、C3−C6アルキニルオキシ基、C3−C6ハロアルケニルオキシ基、C3−C6ハロアルキニルオキシ基、C3−C6アルケニルチオ基、C3−C6アルキニルチオ基、C3−C6ハロアルケニルチオ基、C3−C6ハロアルキニルチオ基、C2−C6アルキルカルボニル基、C2−C6ハロアルキルカルボニル基、C2−C6アルキルカルボニルオキシ基、C2−C6アルキルカルボニルチオ基、C2−C6アルコキシカルボニル基、ヒドロキシ基、C1−C6アルキル基を有していてもよいアミノ基、ペンタフルオロスルファニル基、C3−C9トリアルキルシリル基、C5−C14トリアルキルシリルエチニル基、C1−C4アルキルスルホニル基、C1−C4ハロアルキルスルホニル基、C1−C4アルキルスルフィニル基、C1−C4ハロアルキルスルフィニル基、C2−C5アルコキシアルキル基またはC2−C5アルキルチオアルキル基を表す。〕E is any one of groups selected from the group P 4, tetrazolinone compound according to claim 1, wherein.
Group P 4 : Group consisting of E1 to E7
[In the formula, # represents a bonding position with a tetrazolinone ring, and $ represents a bonding position with Y. Z 1 represents a nitrogen atom or CR 1 ;
Z 2 represents a nitrogen atom or CR 2 ;
Z 3 represents a nitrogen atom or CR 3 ;
Z 4 represents a nitrogen atom or CR 4 ;
Y 1 represents an oxygen atom, a sulfur atom or NR 8 ;
Y 2 represents an oxygen atom, a sulfur atom or NR 6 ;
Y 3 represents an oxygen atom, a sulfur atom or NR 7 ;
R 1 is a hydrogen atom, C1-C6 alkyl group, C3-C6 cycloalkyl group, halogen atom, C1-C6 haloalkyl group, C2-C6 alkenyl group, C1-C6 alkoxy group, C1-C6 alkylthio group, C2-C6. Alkynyl group, nitro group, cyano group, aminocarbonyl group optionally having C1-C6 alkyl group, C2-C6 haloalkenyl group, C2-C6 haloalkynyl group, C3-C6 halocycloalkyl group, C1-C6 Haloalkoxy group, C1-C6 haloalkylthio group, C3-C6 cycloalkyloxy group, C3-C6 halocycloalkyloxy group, C3-C6 cycloalkylthio group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C3 -C6 haloalkenyloxy group, C3-C6 haloalkynyloxy group, C3 -C6 alkenylthio group, C3-C6 alkynylthio group, C3-C6 haloalkenylthio group, C3-C6 haloalkynylthio group, C2-C6 alkylcarbonyl group, C2-C6 haloalkylcarbonyl group, C2-C6 alkylcarbonyloxy group , C2-C6 alkylcarbonylthio group, C2-C6 alkoxycarbonyl group, hydroxy group, thiol group, amino group optionally having C1-C6 alkyl group, pentafluorosulfanyl group, C3-C9 trialkylsilyl group, C5-C14 trialkylsilylethynyl group, C1-C4 alkylsulfonyl group, C1-C4 haloalkylsulfonyl group, C1-C4 alkylsulfinyl group, C1-C4 haloalkylsulfinyl group, C2-C5 alkoxyalkyl group or C2-C5 alkylthio group It represents an alkyl group;
R 2 , R 3 and R 4 are each independently a hydrogen atom, a halogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C2-C3 haloalkenyl group or a C1-C3 alkoxy group. Represents;
R 6 and R 7 each independently represents a hydrogen atom, a C1-C3 alkyl group, a C1-C3 haloalkyl group, a C2-C3 alkenyl group, a C2-C3 haloalkenyl group or a C1-C3 alkoxy group;
R 8 is a hydrogen atom, a C1-C6 alkyl group, a C3-C6 cycloalkyl group, a C1-C6 haloalkyl group, a C2-C6 alkenyl group, a C1-C6 alkoxy group, a C1-C6 alkylthio group, a C2-C6 alkynyl group, Nitro group, cyano group, aminocarbonyl group optionally having C1-C6 alkyl group, C2-C6 haloalkenyl group, C2-C6 haloalkynyl group, C3-C6 halocycloalkyl group, C1-C6 haloalkoxy group , C1-C6 haloalkylthio group, C3-C6 cycloalkyloxy group, C3-C6 halocycloalkyloxy group, C3-C6 cycloalkylthio group, C3-C6 alkenyloxy group, C3-C6 alkynyloxy group, C3-C6 halo Alkenyloxy group, C3-C6 haloalkynyloxy group, C3-C6 alkeni Ruthio group, C3-C6 alkynylthio group, C3-C6 haloalkenylthio group, C3-C6 haloalkynylthio group, C2-C6 alkylcarbonyl group, C2-C6 haloalkylcarbonyl group, C2-C6 alkylcarbonyloxy group, C2- C6 alkylcarbonylthio group, C2-C6 alkoxycarbonyl group, hydroxy group, amino group optionally having C1-C6 alkyl group, pentafluorosulfanyl group, C3-C9 trialkylsilyl group, C5-C14 trialkylsilyl group An ethynyl group, a C1-C4 alkylsulfonyl group, a C1-C4 haloalkylsulfonyl group, a C1-C4 alkylsulfinyl group, a C1-C4 haloalkylsulfinyl group, a C2-C5 alkoxyalkyl group or a C2-C5 alkylthioalkyl group is represented. ]
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013216079 | 2013-10-17 | ||
JP2013216079 | 2013-10-17 | ||
PCT/JP2014/078005 WO2015056811A1 (en) | 2013-10-17 | 2014-10-15 | Tetrazolinone compound and application for same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2015056811A1 true JPWO2015056811A1 (en) | 2017-03-09 |
JP6319317B2 JP6319317B2 (en) | 2018-05-09 |
Family
ID=52828248
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015542920A Active JP6319317B2 (en) | 2013-10-17 | 2014-10-15 | Tetrazolinone compound and use thereof |
Country Status (6)
Country | Link |
---|---|
US (1) | US10077254B2 (en) |
EP (1) | EP3059233B1 (en) |
JP (1) | JP6319317B2 (en) |
CN (1) | CN105636955B (en) |
BR (1) | BR112016008406B1 (en) |
WO (1) | WO2015056811A1 (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2990404B1 (en) | 2013-04-26 | 2020-05-27 | Sumitomo Chemical Company Limited | Tetrazolinone compound and use of same |
EP3020715B1 (en) | 2013-07-12 | 2021-06-16 | Sumitomo Chemical Company Limited | Tetrazolinone compound and use thereof |
CN105593217B (en) | 2013-08-29 | 2018-05-25 | 住友化学株式会社 | Terazololine-one compound and application thereof |
WO2015064727A1 (en) | 2013-10-28 | 2015-05-07 | 住友化学株式会社 | Tetrazolinone compound and application for same |
EP3124485B1 (en) | 2014-03-28 | 2018-11-28 | Sumitomo Chemical Company Limited | Tetrazolinone compounds for controlling pests |
JP6551397B2 (en) | 2014-03-28 | 2019-07-31 | 住友化学株式会社 | Tetrazolinone compound and use thereof |
BR112016021969B1 (en) | 2014-03-28 | 2021-03-23 | Sumitomo Chemical Company, Limited | TETRAZOLINONE COMPOUND, ITS USE, AGENT AND METHOD FOR PEST CONTROL |
Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0881459A (en) * | 1994-07-12 | 1996-03-26 | Nippon Bayeragrochem Kk | 1-pyridyltetrazolinone derivative and herbicide |
JPH0899975A (en) * | 1994-08-05 | 1996-04-16 | Nippon Bayeragrochem Kk | Five-membered heterocyclic ring substituted tetrazolinone derivative and herbicide |
JPH0987281A (en) * | 1995-07-18 | 1997-03-31 | Nissan Chem Ind Ltd | New tetrazolinones and herbicide |
JPH09100277A (en) * | 1995-07-28 | 1997-04-15 | Nissan Chem Ind Ltd | New tetrazolinone derivative and herbicide |
JPH09100272A (en) * | 1995-08-02 | 1997-04-15 | Nippon Bayeragrochem Kk | Herbicidal thiocarbamoyltetrazolinone compound |
JPH09110863A (en) * | 1995-08-10 | 1997-04-28 | Nissan Chem Ind Ltd | New tetrazolinones |
WO1998025912A1 (en) * | 1996-12-13 | 1998-06-18 | E.I. Du Pont De Nemours And Company | Herbicidal heterocyclic amides |
WO1998051683A1 (en) * | 1997-05-15 | 1998-11-19 | E.I. Du Pont De Nemours And Company | Herbicidal tetrazolinones |
JPH11152278A (en) * | 1997-09-11 | 1999-06-08 | E I Du Pont De Nemours & Co | Tetrazoline herbicide |
WO1999048890A1 (en) * | 1998-03-26 | 1999-09-30 | E.I. Du Pont De Nemours And Company | Herbicidal tetrazolinones |
JP2001512460A (en) * | 1997-02-18 | 2001-08-21 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | Herbicidal tetrazolinones |
US6294503B1 (en) * | 1998-12-03 | 2001-09-25 | Ishihara Sangyo Kaisha, Ltd. | Fused heterocycle compounds, process for their preparation, and herbicidal compositions containing them |
CN102875540A (en) * | 2012-10-30 | 2013-01-16 | 南开大学 | Weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996036229A1 (en) * | 1995-05-17 | 1996-11-21 | E.I. Du Pont De Nemours And Company | Fungicidal cyclic amides |
JPH09208565A (en) * | 1996-02-07 | 1997-08-12 | Sumitomo Chem Co Ltd | Tetrazolinone derivative, its use and its production intermediate |
JP2001506984A (en) | 1996-11-26 | 2001-05-29 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | Methyl-substituted fungicides and arthropodicides |
DE19731153A1 (en) * | 1997-07-21 | 1999-01-28 | Basf Ag | 2- (pyrazolyl- and triazolyl-3'-oxymethylene) -phenyl-isoxazolones and -triazolones, processes for their preparation and their use |
AU9206598A (en) * | 1997-09-04 | 1999-03-22 | E.I. Du Pont De Nemours And Company | Enantiomerically enriched compositions and their pesticidal use |
MY160243A (en) * | 2009-09-03 | 2017-02-28 | Bristol Myers Squibb Co | Quinazolines as potassium ion channel inhibitors |
JP6075182B2 (en) | 2012-04-27 | 2017-02-08 | 住友化学株式会社 | Tetrazolinone compounds and uses thereof |
JP6107377B2 (en) | 2012-04-27 | 2017-04-05 | 住友化学株式会社 | Tetrazolinone compounds and uses thereof |
JP6142753B2 (en) | 2012-09-28 | 2017-06-07 | 住友化学株式会社 | Tetrazolinone compounds and uses thereof |
JP6142752B2 (en) | 2012-09-28 | 2017-06-07 | 住友化学株式会社 | Tetrazolinone compounds and uses thereof |
BR112015012209B1 (en) | 2012-11-29 | 2019-07-09 | Sumitomo Chemical Co., Ltd. | TETRAZOLINONE COMPOUND, ITS USE, AGENT AND METHOD FOR PEST CONTROL |
WO2014104382A1 (en) | 2012-12-27 | 2014-07-03 | 住友化学株式会社 | Tetrazolinone compound and applications thereof |
WO2014104268A1 (en) | 2012-12-27 | 2014-07-03 | 住友化学株式会社 | Tetrazolinone compound and applications thereof |
CN104884442B (en) | 2012-12-27 | 2016-11-02 | 住友化学株式会社 | Terazololine-one compound and application thereof |
EP2990404B1 (en) | 2013-04-26 | 2020-05-27 | Sumitomo Chemical Company Limited | Tetrazolinone compound and use of same |
US9675072B2 (en) | 2013-05-29 | 2017-06-13 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and application of same |
EP3020715B1 (en) | 2013-07-12 | 2021-06-16 | Sumitomo Chemical Company Limited | Tetrazolinone compound and use thereof |
BR112016002063B1 (en) | 2013-07-31 | 2021-02-09 | Sumitomo Chemical Company, Limited | tetrazolinone compound, its use, agent and method of pest control |
DK3029038T3 (en) | 2013-07-31 | 2019-05-27 | Sumitomo Chemical Co | TETRAZOLINON CONNECTION AND USE THEREOF |
EP3029035B1 (en) | 2013-07-31 | 2018-05-30 | Sumitomo Chemical Company, Limited | Tetrazolinone compound, and use thereof |
CN105593217B (en) | 2013-08-29 | 2018-05-25 | 住友化学株式会社 | Terazololine-one compound and application thereof |
WO2015041360A1 (en) | 2013-09-20 | 2015-03-26 | 住友化学株式会社 | Tetrazolinone compound and use thereof |
WO2015046480A1 (en) | 2013-09-25 | 2015-04-02 | 住友化学株式会社 | Tetrazolinone compound and use thereof |
US10085450B2 (en) | 2013-10-17 | 2018-10-02 | Sumitomo Chemical Company, Limited | Tetrazolinone compound and use thereof |
BR112016008160B1 (en) | 2013-10-25 | 2020-12-08 | Sumitomo Chemical Company, Limited | tetrazolinone compound, its use, agent and process of pest control |
-
2014
- 2014-10-15 BR BR112016008406-3A patent/BR112016008406B1/en active IP Right Grant
- 2014-10-15 EP EP14853630.3A patent/EP3059233B1/en active Active
- 2014-10-15 JP JP2015542920A patent/JP6319317B2/en active Active
- 2014-10-15 WO PCT/JP2014/078005 patent/WO2015056811A1/en active Application Filing
- 2014-10-15 CN CN201480056941.5A patent/CN105636955B/en active Active
- 2014-10-15 US US15/029,377 patent/US10077254B2/en active Active
Patent Citations (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0881459A (en) * | 1994-07-12 | 1996-03-26 | Nippon Bayeragrochem Kk | 1-pyridyltetrazolinone derivative and herbicide |
JPH0899975A (en) * | 1994-08-05 | 1996-04-16 | Nippon Bayeragrochem Kk | Five-membered heterocyclic ring substituted tetrazolinone derivative and herbicide |
JPH0987281A (en) * | 1995-07-18 | 1997-03-31 | Nissan Chem Ind Ltd | New tetrazolinones and herbicide |
JPH09100277A (en) * | 1995-07-28 | 1997-04-15 | Nissan Chem Ind Ltd | New tetrazolinone derivative and herbicide |
JPH09100272A (en) * | 1995-08-02 | 1997-04-15 | Nippon Bayeragrochem Kk | Herbicidal thiocarbamoyltetrazolinone compound |
JPH09110863A (en) * | 1995-08-10 | 1997-04-28 | Nissan Chem Ind Ltd | New tetrazolinones |
WO1998025912A1 (en) * | 1996-12-13 | 1998-06-18 | E.I. Du Pont De Nemours And Company | Herbicidal heterocyclic amides |
JP2001512460A (en) * | 1997-02-18 | 2001-08-21 | イー・アイ・デユポン・ドウ・ヌムール・アンド・カンパニー | Herbicidal tetrazolinones |
WO1998051683A1 (en) * | 1997-05-15 | 1998-11-19 | E.I. Du Pont De Nemours And Company | Herbicidal tetrazolinones |
JPH11152278A (en) * | 1997-09-11 | 1999-06-08 | E I Du Pont De Nemours & Co | Tetrazoline herbicide |
WO1999048890A1 (en) * | 1998-03-26 | 1999-09-30 | E.I. Du Pont De Nemours And Company | Herbicidal tetrazolinones |
US6294503B1 (en) * | 1998-12-03 | 2001-09-25 | Ishihara Sangyo Kaisha, Ltd. | Fused heterocycle compounds, process for their preparation, and herbicidal compositions containing them |
CN102875540A (en) * | 2012-10-30 | 2013-01-16 | 南开大学 | Weeding activity of 2-benzoxazinone-5-cyclohexylaminocarbonyltetrazolylone |
Also Published As
Publication number | Publication date |
---|---|
BR112016008406B1 (en) | 2021-02-23 |
US20160272622A1 (en) | 2016-09-22 |
US10077254B2 (en) | 2018-09-18 |
EP3059233A1 (en) | 2016-08-24 |
EP3059233B1 (en) | 2017-12-20 |
CN105636955B (en) | 2018-01-12 |
EP3059233A4 (en) | 2017-04-05 |
WO2015056811A1 (en) | 2015-04-23 |
JP6319317B2 (en) | 2018-05-09 |
CN105636955A (en) | 2016-06-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US9554576B2 (en) | Tetrazolinone compounds and their use as pesticides | |
JP6323450B2 (en) | Tetrazolinone compounds and uses thereof | |
JP6350534B2 (en) | Tetrazolinone compounds and uses thereof | |
JP6075182B2 (en) | Tetrazolinone compounds and uses thereof | |
JP6142752B2 (en) | Tetrazolinone compounds and uses thereof | |
JP6319317B2 (en) | Tetrazolinone compound and use thereof | |
JP6432517B2 (en) | Tetrazolinone compounds and uses thereof | |
BR112015012209B1 (en) | TETRAZOLINONE COMPOUND, ITS USE, AGENT AND METHOD FOR PEST CONTROL | |
BR112016004003B1 (en) | tetrazolinone compound and its use | |
BR112016001979B1 (en) | TETRAZOLINONE AND PIRAZOL COMPOUNDS, USES OF THE SAME, AGENT AND METHOD FOR PEST CONTROL | |
JPWO2015016373A1 (en) | Tetrazolinone compounds and uses thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20170728 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20180306 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20180319 |
|
R151 | Written notification of patent or utility model registration |
Ref document number: 6319317 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R151 |
|
S531 | Written request for registration of change of domicile |
Free format text: JAPANESE INTERMEDIATE CODE: R313531 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |